# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2007 # 1. SUBMISSION DETAILS _publ_requested_journal Org.Biomol.Chem. _publ_contact_author_name ' Michael S. Sherburn ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_author_email 'sherburn@rsc.anu.edu.au ' _publ_contact_author_phone ' 61 2 6125 4988 ' _publ_contact_author_fax ' 61 2 6125 8114 ' loop_ _publ_author_name _publ_author_address 'Pearson, Emma L.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Willis, Anthony C.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Sherburn, Michael S.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Paddon-Row, Michael N.' ; School of Chemistry, University of New South Wales, Sydney, N. S. W. 2052, Australia ; _audit_creation_date 05-09-05 _audit_creation_method CRYSTALS_ver_12-03-99 # 5091633 she0509 _audit_update_record ; 2005-05-09 - Report on C15 H13 Br O4 by Anthony C. Willis for Craig Turner and Mick Sherburn 2005-05-10 - passes checkcif tests with minor warnings ; _publ_requested_category ' fo ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Controlling cis/trans-selectivity in intramolecular Diels--Alder reactions of benzo-tethered, ester linked 1,3,9-decatrienes ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~15~H~13~BrO~4~ is reported. ; _publ_section_comment #Text of the paper ; The crystallographic asymmetric unit consists of one C~15~H~13~BrO~4~ molecule. The largest features in the final difference electron density map are adjacent to the Br atom. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; Hydrogen atoms were included at calculated positions and during refinement they ride on the atom to which they are attached. ; _publ_section_exptl_prep ; The compound was prepared by CIT and recrystallized from ethylacetate/heptane. The sample ID is L160maj. ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; #============================================================= _cell_length_a 6.7091(2) _cell_angle_alpha 103.9603(17) _cell_length_b 8.0770(2) _cell_angle_beta 93.8881(18) _cell_length_c 13.7233(4) _cell_angle_gamma 109.0036(18) _cell_volume 673.62(3) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'Br ' -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C15 H13 Br O4 ' _chemical_formula_moiety ' C15 H13 Br O4 ' _chemical_compound_source ; ? ; _chemical_formula_weight 337.17 _cell_measurement_reflns_used 7773 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 200 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_max 0.32 _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 3.061 _diffrn_measurement_device_type ; Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 2.0 deg at rate 50 sec/frame, crystal-detector distance 25mm, multiple scan sets so over 95 percent of data collected with 2-fold redundancy or more. ; # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 10 0 0 0.170 0 1 0 0.050 0 -1 0 0.030 1 4 0 0.052 0 1 -6 0.088 0 -1 6 0.106 -2 1 -1 0.158 2 -3 -3 0.110 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.497 _exptl_absorpt_correction_T_max 0.803 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; #_diffrn_reflns_av_R_equivalents 0.032 # Sheldrick geometric definitions 0.56 0.78 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 200 _diffrn_reflns_number 11941 _reflns_number_total 3101 _diffrn_reflns_av_R_equivalents 0.03 # Number of reflections with Friedels Law is 3101 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3097 _diffrn_reflns_theta_min 2.778 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -10 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _refine_diff_density_min -0.64 _refine_diff_density_max 0.27 _refine_ls_number_reflns 2507 _refine_ls_number_restraints 0 _refine_ls_number_parameters 181 #_refine_ls_R_factor_ref 0.0272 _refine_ls_wR_factor_ref 0.0321 _refine_ls_goodness_of_fit_ref 1.0615 #_reflns_number_all 3094 _refine_ls_R_factor_all 0.0345 _refine_ls_wR_factor_all 0.0356 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 2507 _refine_ls_R_factor_gt 0.0272 _refine_ls_wR_factor_gt 0.0321 _refine_ls_shift/su_max 0.000821 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.05 0.191 0.722 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Altomare, A., Cascarano, G., Giacovazzo C., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Br1 Br 0.55757(4) 0.81720(3) 0.234293(17) 0.0380 1.0000 Uani . . . . . . O1 O 1.0645(2) 0.5919(2) 0.35489(12) 0.0358 1.0000 Uani . . . . . . O2 O 1.0929(2) 0.3853(2) 0.22568(13) 0.0433 1.0000 Uani . . . . . . O3 O 0.3292(3) 0.1305(2) 0.02360(12) 0.0435 1.0000 Uani . . . . . . O4 O 0.3482(2) 0.07961(18) 0.17621(11) 0.0306 1.0000 Uani . . . . . . C1 C 0.6418(3) 0.6090(2) 0.20050(15) 0.0266 1.0000 Uani . . . . . . C2 C 0.6247(3) 0.5032(2) 0.27903(14) 0.0239 1.0000 Uani . . . . . . C3 C 0.7237(3) 0.6214(2) 0.38577(14) 0.0264 1.0000 Uani . . . . . . C4 C 0.6092(3) 0.6920(3) 0.45465(16) 0.0353 1.0000 Uani . . . . . . C5 C 0.7087(4) 0.8006(3) 0.55186(17) 0.0431 1.0000 Uani . . . . . . C6 C 0.9246(4) 0.8393(3) 0.58126(17) 0.0450 1.0000 Uani . . . . . . C7 C 1.0409(4) 0.7682(3) 0.51500(17) 0.0398 1.0000 Uani . . . . . . C8 C 0.9377(3) 0.6589(3) 0.41871(15) 0.0301 1.0000 Uani . . . . . . C9 C 0.9755(3) 0.4445(3) 0.27259(16) 0.0299 1.0000 Uani . . . . . . C10 C 0.7327(3) 0.3611(2) 0.24805(14) 0.0249 1.0000 Uani . . . . . . C11 C 0.6695(3) 0.2596(2) 0.13444(14) 0.0268 1.0000 Uani . . . . . . C12 C 0.7442(3) 0.3918(3) 0.07024(15) 0.0318 1.0000 Uani . . . . . . C13 C 0.6958(3) 0.5631(3) 0.10938(15) 0.0299 1.0000 Uani . . . . . . C14 C 0.4307(3) 0.1535(2) 0.10434(14) 0.0272 1.0000 Uani . . . . . . C15 C 0.1262(3) -0.0402(3) 0.14887(19) 0.0389 1.0000 Uani . . . . . . H21 H 0.4690 0.4441 0.28027 0.0281 1.0000 Uiso R . . . . . H41 H 0.4534 0.6642 0.43395 0.0406 1.0000 Uiso R . . . . . H51 H 0.6247 0.8509 0.60066 0.0493 1.0000 Uiso R . . . . . H61 H 0.9963 0.9192 0.65094 0.0494 1.0000 Uiso R . . . . . H71 H 1.1963 0.7950 0.53599 0.0444 1.0000 Uiso R . . . . . H101 H 0.6806 0.2735 0.28918 0.0299 1.0000 Uiso R . . . . . H111 H 0.7427 0.1684 0.12094 0.0318 1.0000 Uiso R . . . . . H121 H 0.9018 0.4250 0.07206 0.0378 1.0000 Uiso R . . . . . H122 H 0.6698 0.3307 -0.00147 0.0378 1.0000 Uiso R . . . . . H131 H 0.7047 0.6457 0.06477 0.0347 1.0000 Uiso R . . . . . H151 H 0.0791 -0.0886 0.20727 0.0426 1.0000 Uiso R . . . . . H152 H 0.1106 -0.1441 0.08829 0.0426 1.0000 Uiso R . . . . . H153 H 0.0360 0.0294 0.13221 0.0426 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.04138(13) 0.02900(11) 0.04597(13) 0.00966(8) -0.00111(8) 0.01761(8) O1 0.0204(6) 0.0400(8) 0.0393(8) 0.0017(6) -0.0023(5) 0.0088(6) O2 0.0261(7) 0.0471(9) 0.0529(10) 0.0022(7) 0.0023(7) 0.0171(6) O3 0.0361(8) 0.0471(9) 0.0373(8) 0.0123(7) -0.0072(6) 0.0039(7) O4 0.0233(6) 0.0279(7) 0.0372(7) 0.0092(6) 0.0022(5) 0.0050(5) C1 0.0224(8) 0.0226(8) 0.0330(9) 0.0079(7) -0.0011(7) 0.0065(7) C2 0.0191(7) 0.0240(8) 0.0271(8) 0.0072(7) 0.0007(6) 0.0060(6) C3 0.0256(9) 0.0250(8) 0.0273(9) 0.0087(7) 0.0024(7) 0.0066(7) C4 0.0315(10) 0.0368(11) 0.0332(10) 0.0052(8) 0.0052(8) 0.0097(8) C5 0.0452(12) 0.0453(13) 0.0327(11) 0.0036(9) 0.0097(9) 0.0124(10) C6 0.0501(13) 0.0443(13) 0.0292(10) 0.0029(9) -0.0034(9) 0.0093(10) C7 0.0350(11) 0.0410(12) 0.0350(11) 0.0057(9) -0.0074(9) 0.0085(9) C8 0.0269(9) 0.0305(9) 0.0312(9) 0.0092(7) -0.0004(7) 0.0083(7) C9 0.0231(8) 0.0307(9) 0.0357(10) 0.0095(8) 0.0006(7) 0.0099(7) C10 0.0208(8) 0.0249(8) 0.0292(9) 0.0087(7) 0.0015(7) 0.0077(7) C11 0.0240(8) 0.0244(8) 0.0311(9) 0.0056(7) 0.0025(7) 0.0093(7) C12 0.0306(9) 0.0345(10) 0.0296(9) 0.0099(8) 0.0069(8) 0.0094(8) C13 0.0260(9) 0.0298(9) 0.0311(9) 0.0121(7) 0.0000(7) 0.0043(7) C14 0.0270(9) 0.0211(8) 0.0311(9) 0.0037(7) 0.0010(7) 0.0085(7) C15 0.0246(9) 0.0329(10) 0.0489(12) 0.0033(9) 0.0059(9) 0.0027(8) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 . C1 . 1.9081(18) yes O1 . C8 . 1.398(3) yes O1 . C9 . 1.359(2) yes O2 . C9 . 1.195(3) yes O3 . C14 . 1.201(2) yes O4 . C14 . 1.334(2) yes O4 . C15 . 1.451(2) yes C1 . C2 . 1.517(3) yes C1 . C13 . 1.326(3) yes C2 . C3 . 1.510(2) yes C2 . C10 . 1.540(2) yes C2 . H21 . 1.000 no C3 . C4 . 1.390(3) yes C3 . C8 . 1.386(3) yes C4 . C5 . 1.389(3) yes C4 . H41 . 1.000 no C5 . C6 . 1.387(4) yes C5 . H51 . 1.000 no C6 . C7 . 1.379(4) yes C6 . H61 . 1.000 no C7 . C8 . 1.386(3) yes C7 . H71 . 1.000 no C9 . C10 . 1.524(2) yes C10 . C11 . 1.533(3) yes C10 . H101 . 1.000 no C11 . C12 . 1.528(3) yes C11 . C14 . 1.522(3) yes C11 . H111 . 1.000 no C12 . C13 . 1.505(3) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C13 . H131 . 1.000 no C15 . H151 . 1.000 no C15 . H152 . 1.000 no C15 . H153 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C8 . O1 . C9 . 121.07(15) yes C14 . O4 . C15 . 115.39(16) yes Br1 . C1 . C2 . 115.87(13) yes Br1 . C1 . C13 . 117.94(14) yes C2 . C1 . C13 . 126.03(17) yes C1 . C2 . C3 . 113.77(15) yes C1 . C2 . C10 . 108.78(15) yes C3 . C2 . C10 . 109.17(14) yes C1 . C2 . H21 . 106.912 no C3 . C2 . H21 . 106.516 no C10 . C2 . H21 . 111.714 no C2 . C3 . C4 . 123.17(17) yes C2 . C3 . C8 . 119.17(17) yes C4 . C3 . C8 . 117.65(18) yes C3 . C4 . C5 . 120.7(2) yes C3 . C4 . H41 . 119.628 no C5 . C4 . H41 . 119.630 no C4 . C5 . C6 . 120.0(2) yes C4 . C5 . H51 . 120.004 no C6 . C5 . H51 . 120.007 no C5 . C6 . C7 . 120.4(2) yes C5 . C6 . H61 . 119.805 no C7 . C6 . H61 . 119.807 no C6 . C7 . C8 . 118.6(2) yes C6 . C7 . H71 . 120.704 no C8 . C7 . H71 . 120.705 no O1 . C8 . C7 . 115.86(18) yes O1 . C8 . C3 . 121.52(17) yes C7 . C8 . C3 . 122.6(2) yes O1 . C9 . O2 . 117.80(17) yes O1 . C9 . C10 . 118.05(17) yes O2 . C9 . C10 . 124.12(18) yes C2 . C10 . C9 . 112.75(15) yes C2 . C10 . C11 . 111.90(14) yes C9 . C10 . C11 . 108.42(15) yes C2 . C10 . H101 . 105.111 no C9 . C10 . H101 . 108.829 no C11 . C10 . H101 . 109.735 no C10 . C11 . C12 . 110.53(15) yes C10 . C11 . C14 . 112.55(15) yes C12 . C11 . C14 . 110.49(15) yes C10 . C11 . H111 . 106.952 no C12 . C11 . H111 . 109.155 no C14 . C11 . H111 . 106.991 no C11 . C12 . C13 . 111.62(16) yes C11 . C12 . H121 . 108.934 no C13 . C12 . H121 . 108.932 no C11 . C12 . H122 . 108.933 no C13 . C12 . H122 . 108.934 no H121 . C12 . H122 . 109.467 no C12 . C13 . C1 . 122.77(18) yes C12 . C13 . H131 . 118.613 no C1 . C13 . H131 . 118.614 no C11 . C14 . O4 . 112.01(15) yes C11 . C14 . O3 . 124.45(18) yes O4 . C14 . O3 . 123.44(18) yes O4 . C15 . H151 . 109.466 no O4 . C15 . H152 . 109.467 no H151 . C15 . H152 . 109.476 no O4 . C15 . H153 . 109.467 no H151 . C15 . H153 . 109.476 no H152 . C15 . H153 . 109.476 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Br1 O4 3.115(2) . 1_565 no O1 C4 3.570(2) . 1_655 no O2 C2 3.357(2) . 1_655 no O2 O4 3.405(2) . 1_655 no O2 C15 3.429(3) . 1_655 no O2 C6 3.542(3) . 2_766 no O3 C11 3.370(2) . 2_655 no O3 C14 3.433(3) . 2_655 no O3 C13 3.448(3) . 2_665 no O3 C15 3.493(3) . 2 no O3 O3 3.578(4) . 2_655 no C4 C4 3.531(5) . 2_666 no C6 C9 3.572(4) . 2_766 no C13 C15 3.438(3) . 1_665 no C13 C13 3.559(4) . 2_665 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Br1 C1 C2 C3 . . . . -48.8(2) no Br1 C1 C2 C10 . . . . -170.7(1) no Br1 C1 C13 C12 . . . . -173.9(1) no O1 C8 C3 C2 . . . . 0.9(3) no O1 C8 C3 C4 . . . . 179.3(2) no O1 C8 C7 C6 . . . . 179.6(2) no O1 C9 C10 C2 . . . . 31.3(3) no O1 C9 C10 C11 . . . . 155.7(2) no O2 C9 O1 C8 . . . . -174.3(2) no O2 C9 C10 C2 . . . . -150.9(2) no O2 C9 C10 C11 . . . . -26.5(3) no O3 C14 O4 C15 . . . . 2.9(3) no O3 C14 C11 C10 . . . . 146.5(2) no O3 C14 C11 C12 . . . . 22.4(3) no O4 C14 C11 C10 . . . . -37.0(2) no O4 C14 C11 C12 . . . . -161.2(2) no C1 C2 C3 C4 . . . . 92.5(2) no C1 C2 C3 C8 . . . . -89.1(2) no C1 C2 C10 C9 . . . . 77.7(2) no C1 C2 C10 C11 . . . . -44.8(2) no C1 C13 C12 C11 . . . . 14.5(2) no C2 C1 C13 C12 . . . . 1.4(3) no C2 C3 C4 C5 . . . . -179.8(2) no C2 C3 C8 C7 . . . . 179.1(2) no C2 C10 C11 C12 . . . . 62.7(2) no C2 C10 C11 C14 . . . . -61.4(2) no C3 C2 C1 C13 . . . . 135.9(2) no C3 C2 C10 C9 . . . . -47.0(2) no C3 C2 C10 C11 . . . . -169.6(1) no C3 C4 C5 C6 . . . . -0.2(4) no C3 C8 O1 C9 . . . . -21.4(3) no C3 C8 C7 C6 . . . . 1.4(4) no C4 C3 C2 C10 . . . . -145.7(2) no C4 C3 C8 C7 . . . . -2.5(3) no C4 C5 C6 C7 . . . . -1.0(4) no C5 C4 C3 C8 . . . . 1.9(3) no C5 C6 C7 C8 . . . . 0.4(4) no C7 C8 O1 C9 . . . . 160.3(2) no C8 O1 C9 C10 . . . . 3.6(3) no C8 C3 C2 C10 . . . . 32.6(2) no C9 C10 C11 C12 . . . . -62.2(2) no C9 C10 C11 C14 . . . . 173.7(2) no C10 C2 C1 C13 . . . . 13.9(2) no C10 C11 C12 C13 . . . . -45.0(2) no C11 C14 O4 C15 . . . . -173.6(2) no C13 C12 C11 C14 . . . . 80.3(2) no #------------------------------------------------------------------------------ #===END data_she0708 # # 1. SUBMISSION DETAILS _publ_requested_journal Org.Biomol.Chem. _publ_contact_author_name ' Michael S. Sherburn ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_author_email 'sherburn@rsc.anu.edu.au ' _publ_contact_author_phone ' 61 2 6125 4988 ' _publ_contact_author_fax ' 61 2 6125 8114 ' loop_ _publ_author_name _publ_author_address 'Pearson, Emma L.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Willis, Anthony C.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Sherburn, Michael S.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Paddon-Row, Michael N.' ; School of Chemistry, University of New South Wales, Sydney, N. S. W. 2052, Australia ; _audit_creation_date 07-05-25 _audit_creation_method CRYSTALS_ver_12.18 _audit_update_record ; 2007-05-25 - Report on C18 H22 O4 Si by Anthony C. Willis for Emma Pearson and Mick Sherburn 2007-05-25 - passes checkcif tests with minor warnings ; _oxford_structure_analysis_title '5250951 she0708' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 44.1595(17) _cell_length_b 6.5892(2) _cell_length_c 30.3735(11) _cell_angle_alpha 90 _cell_angle_beta 127.2050(11) _cell_angle_gamma 90 _cell_volume 7039.2(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Si 0.0817 0.0704 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937 1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 16 # Given Formula = C18 H22 O4 Si1 # Dc = 1.25 Fooo = 2816.00 Mu = 1.50 M = 660.91 # Found Formula = C18 H22 O4 Si1 # Dc = 1.25 FOOO = 2816.00 Mu = 1.50 M = 660.91 _chemical_formula_sum 'C18 H22 O4 Si' _chemical_formula_moiety 'C18 H22 O4 Si' _chemical_compound_source local _chemical_formula_weight 330.46 _cell_measurement_reflns_used 97814 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 25 _cell_measurement_temperature 200 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_meas ' not measured ' # Non-dispersive F(000): _exptl_crystal_F_000 2816 _exptl_absorpt_coefficient_mu 0.150 # Sheldrick geometric approximatio 0.98 0.99 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.080 -1 0 0 0.030 0 1 0 0.240 0 -1 0 0.260 0 0 1 0.070 0 0 -1 0.030 -3 0 3 0.060 3 0 -3 0.060 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.053 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 1.5 deg at rate 150 sec/frame, crystal-detector distance 45mm, multiple scan sets so over 90 percent of data collected with 4-fold redundancy or more. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Watkin et al 2003)' _computing_publication_material 'CRYSTALS (Watkin et al 2003)' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 48216 _reflns_number_total 6112 _diffrn_reflns_av_R_equivalents 0.079 # Number of reflections with Friedels Law is 6112 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6180 _diffrn_reflns_theta_min 2.556 _diffrn_reflns_theta_max 24.972 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 24.97 # 21.476 _diffrn_measured_fraction_theta_full 0.990 # 0.995 _diffrn_reflns_limit_h_min -52 _diffrn_reflns_limit_h_max 51 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _reflns_limit_h_min -52 _reflns_limit_h_max 41 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 36 _oxford_diffrn_Wilson_B_factor 3.48 _oxford_diffrn_Wilson_scale 30.37 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.21 _refine_diff_density_max 0.22 _refine_ls_number_reflns 3703 _refine_ls_number_restraints 0 _refine_ls_number_parameters 415 #_refine_ls_R_factor_ref 0.0394 _refine_ls_wR_factor_ref 0.0410 _refine_ls_goodness_of_fit_ref 1.1512 #_reflns_number_all 6088 _refine_ls_R_factor_all 0.0761 _refine_ls_wR_factor_all 0.0487 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3703 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_gt 0.0410 _refine_ls_shift/su_max 0.000318 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.891 -0.393 0.752 -0.241 0.197 ; _publ_requested_category ' fo ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Controlling cis/trans-selectivity in intramolecular Diels--Alder reactions of benzo-tethered, ester linked 1,3,9-decatrienes ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~18~H~22~O~4~Si is reported. ; _publ_section_comment #Text of the paper ; The crystallographic asymmetric unit consists of two C~18~H~22~O~4~Si molecules. Hydrogen atoms were observed in difference electron density maps prior to their inclusion. They were introduced at calculated positions and during refinement they ride of the atom to which they are attached. The largest features in a final difference electron density map are located on C---Si and C---C bonds and have no chemical significance. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; Hydrogen atoms ride of the atom to which they are attached. ; _publ_section_exptl_prep ; The compound was prepared by ELP and recrystallized from dichloromethane/chloroform/heptane. The sample id. was EP-I-125at02. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Mackay, S., Gilmore, C. J., Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Si20 Si 0.17712(2) 0.46261(13) 0.42486(3) 0.0540 1.0000 Uani . . . . . . Si120 Si 0.187125(19) 0.87311(12) 0.13985(3) 0.0452 1.0000 Uani . . . . . . O1 O 0.07027(6) 0.7644(3) 0.36886(8) 0.0594 1.0000 Uani . . . . . . O15 O 0.05343(6) 0.9219(3) 0.29362(9) 0.0730 1.0000 Uani . . . . . . O17 O 0.07503(6) 0.2730(3) 0.21828(9) 0.0677 1.0000 Uani . . . . . . O18 O 0.01575(5) 0.3261(3) 0.18949(8) 0.0591 1.0000 Uani . . . . . . O101 O 0.14604(5) 1.3007(3) 0.21398(7) 0.0490 1.0000 Uani . . . . . . O115 O 0.09600(5) 1.4363(3) 0.13932(8) 0.0599 1.0000 Uani . . . . . . O117 O 0.03646(6) 0.7801(3) 0.02267(9) 0.0736 1.0000 Uani . . . . . . O118 O 0.03281(5) 0.8069(3) 0.09251(8) 0.0534 1.0000 Uani . . . . . . C2 C 0.06061(8) 0.7627(5) 0.31674(12) 0.0532 1.0000 Uani . . . . . . C3 C 0.05963(7) 0.5577(4) 0.29350(10) 0.0432 1.0000 Uani . . . . . . C4 C 0.05975(7) 0.5835(4) 0.24317(10) 0.0454 1.0000 Uani . . . . . . C5 C 0.09713(7) 0.6776(4) 0.26036(10) 0.0502 1.0000 Uani . . . . . . C6 C 0.13082(7) 0.6280(4) 0.31878(10) 0.0479 1.0000 Uani . . . . . . C7 C 0.13093(7) 0.5179(4) 0.35564(10) 0.0424 1.0000 Uani . . . . . . C8 C 0.09319(6) 0.4263(4) 0.33866(9) 0.0405 1.0000 Uani . . . . . . C9 C 0.09009(7) 0.4135(4) 0.38547(10) 0.0456 1.0000 Uani . . . . . . C10 C 0.09703(8) 0.2388(5) 0.41541(11) 0.0565 1.0000 Uani . . . . . . C11 C 0.09335(8) 0.2406(6) 0.45810(12) 0.0677 1.0000 Uani . . . . . . C12 C 0.08294(9) 0.4160(6) 0.47064(13) 0.0732 1.0000 Uani . . . . . . C13 C 0.07542(8) 0.5886(6) 0.44051(12) 0.0651 1.0000 Uani . . . . . . C14 C 0.07859(7) 0.5841(4) 0.39815(11) 0.0502 1.0000 Uani . . . . . . C16 C 0.05222(7) 0.3787(4) 0.21608(10) 0.0460 1.0000 Uani . . . . . . C19 C 0.00499(9) 0.1288(5) 0.16364(13) 0.0684 1.0000 Uani . . . . . . C21 C 0.17951(9) 0.5708(6) 0.48390(12) 0.0752 1.0000 Uani . . . . . . C22 C 0.18463(10) 0.1817(6) 0.43327(16) 0.0872 1.0000 Uani . . . . . . C23 C 0.21700(8) 0.5801(6) 0.42806(12) 0.0715 1.0000 Uani . . . . . . C102 C 0.11129(7) 1.2829(4) 0.16359(11) 0.0439 1.0000 Uani . . . . . . C103 C 0.09591(6) 1.0709(4) 0.14421(10) 0.0382 1.0000 Uani . . . . . . C104 C 0.06320(7) 1.0748(4) 0.08215(10) 0.0431 1.0000 Uani . . . . . . C105 C 0.07779(7) 1.1452(4) 0.04982(11) 0.0503 1.0000 Uani . . . . . . C106 C 0.11774(7) 1.0770(4) 0.07527(10) 0.0462 1.0000 Uani . . . . . . C107 C 0.14112(7) 0.9743(4) 0.12257(10) 0.0395 1.0000 Uani . . . . . . C108 C 0.12781(6) 0.9254(4) 0.15779(9) 0.0363 1.0000 Uani . . . . . . C109 C 0.15886(6) 0.9406(4) 0.21953(9) 0.0385 1.0000 Uani . . . . . . C110 C 0.18042(7) 0.7778(4) 0.25311(10) 0.0434 1.0000 Uani . . . . . . C111 C 0.20875(7) 0.8052(5) 0.30930(11) 0.0529 1.0000 Uani . . . . . . C112 C 0.21540(8) 0.9943(5) 0.33300(11) 0.0559 1.0000 Uani . . . . . . C113 C 0.19362(7) 1.1571(4) 0.30079(11) 0.0528 1.0000 Uani . . . . . . C114 C 0.16595(7) 1.1282(4) 0.24454(10) 0.0428 1.0000 Uani . . . . . . C116 C 0.04337(7) 0.8706(4) 0.06187(11) 0.0458 1.0000 Uani . . . . . . C119 C 0.01273(8) 0.6154(4) 0.07616(13) 0.0637 1.0000 Uani . . . . . . C121 C 0.22976(7) 0.9733(4) 0.20673(11) 0.0534 1.0000 Uani . . . . . . C122 C 0.18501(8) 0.5892(4) 0.14010(13) 0.0610 1.0000 Uani . . . . . . C123 C 0.19206(8) 0.9519(6) 0.08524(12) 0.0675 1.0000 Uani . . . . . . H31 H 0.03548 0.4879 0.28086 0.0520 1.0000 Uiso R . . . . . H41 H 0.03849 0.6769 0.21623 0.0538 1.0000 Uiso R . . . . . H51 H 0.09399 0.8284 0.25690 0.0617 1.0000 Uiso R . . . . . H52 H 0.10250 0.6269 0.23468 0.0617 1.0000 Uiso R . . . . . H61 H 0.15590 0.6840 0.33123 0.0578 1.0000 Uiso R . . . . . H81 H 0.09039 0.2869 0.32359 0.0491 1.0000 Uiso R . . . . . H101 H 0.10467 0.1113 0.40663 0.0660 1.0000 Uiso R . . . . . H111 H 0.09831 0.1139 0.47964 0.0801 1.0000 Uiso R . . . . . H121 H 0.08088 0.4170 0.50167 0.0939 1.0000 Uiso R . . . . . H131 H 0.06773 0.7162 0.44916 0.0822 1.0000 Uiso R . . . . . H191 H -0.02265 0.1054 0.14512 0.0728 1.0000 Uiso R . . . . . H192 H 0.02030 0.0219 0.19235 0.0728 1.0000 Uiso R . . . . . H193 H 0.00988 0.1223 0.13553 0.0728 1.0000 Uiso R . . . . . H211 H 0.20463 0.5366 0.51951 0.0875 1.0000 Uiso R . . . . . H212 H 0.17655 0.7216 0.47987 0.0875 1.0000 Uiso R . . . . . H213 H 0.15862 0.5119 0.48386 0.0875 1.0000 Uiso R . . . . . H221 H 0.20919 0.1514 0.47008 0.1012 1.0000 Uiso R . . . . . H222 H 0.16323 0.1165 0.43091 0.1012 1.0000 Uiso R . . . . . H223 H 0.18546 0.1270 0.40331 0.1012 1.0000 Uiso R . . . . . H231 H 0.24166 0.5510 0.46486 0.0807 1.0000 Uiso R . . . . . H232 H 0.21308 0.7302 0.42285 0.0807 1.0000 Uiso R . . . . . H233 H 0.21756 0.5218 0.39816 0.0807 1.0000 Uiso R . . . . . H1031 H 0.08572 1.0232 0.16419 0.0472 1.0000 Uiso R . . . . . H1041 H 0.04414 1.1766 0.07585 0.0509 1.0000 Uiso R . . . . . H1051 H 0.07708 1.2969 0.04832 0.0586 1.0000 Uiso R . . . . . H1052 H 0.06059 1.0895 0.01144 0.0586 1.0000 Uiso R . . . . . H1061 H 0.12799 1.1122 0.05454 0.0577 1.0000 Uiso R . . . . . H1081 H 0.11755 0.7839 0.14909 0.0442 1.0000 Uiso R . . . . . H1101 H 0.17552 0.6391 0.23668 0.0544 1.0000 Uiso R . . . . . H1111 H 0.22447 0.6869 0.33277 0.0644 1.0000 Uiso R . . . . . H1121 H 0.23597 1.0131 0.37344 0.0642 1.0000 Uiso R . . . . . H1131 H 0.19768 1.2942 0.31770 0.0623 1.0000 Uiso R . . . . . H1191 H 0.00614 0.5816 0.10154 0.0701 1.0000 Uiso R . . . . . H1192 H -0.01110 0.6261 0.03740 0.0701 1.0000 Uiso R . . . . . H1193 H 0.02927 0.5062 0.07822 0.0701 1.0000 Uiso R . . . . . H1211 H 0.25329 0.9152 0.21391 0.0654 1.0000 Uiso R . . . . . H1212 H 0.23035 1.1246 0.20475 0.0654 1.0000 Uiso R . . . . . H1213 H 0.22848 0.9338 0.23736 0.0654 1.0000 Uiso R . . . . . H1221 H 0.20914 0.5315 0.14918 0.0744 1.0000 Uiso R . . . . . H1222 H 0.18176 0.5442 0.16845 0.0744 1.0000 Uiso R . . . . . H1223 H 0.16301 0.5404 0.10279 0.0744 1.0000 Uiso R . . . . . H1231 H 0.21649 0.8979 0.09459 0.0853 1.0000 Uiso R . . . . . H1232 H 0.19206 1.1034 0.08330 0.0853 1.0000 Uiso R . . . . . H1233 H 0.17028 0.8965 0.04869 0.0853 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si20 0.0422(4) 0.0695(5) 0.0453(4) 0.0069(4) 0.0238(3) 0.0030(4) Si120 0.0386(4) 0.0509(4) 0.0506(4) -0.0047(3) 0.0293(3) -0.0017(3) O1 0.0749(13) 0.0564(12) 0.0559(11) -0.0055(10) 0.0444(11) 0.0058(10) O15 0.0933(16) 0.0562(14) 0.0672(13) 0.0065(11) 0.0474(13) 0.0192(12) O17 0.0601(12) 0.0758(14) 0.0809(14) -0.0226(12) 0.0498(12) -0.0036(11) O18 0.0426(10) 0.0540(12) 0.0627(12) -0.0049(10) 0.0224(9) 0.0002(9) O101 0.0457(10) 0.0370(10) 0.0551(11) -0.0092(8) 0.0256(9) -0.0064(8) O115 0.0558(11) 0.0359(11) 0.0743(13) 0.0025(10) 0.0322(10) 0.0035(9) O117 0.0774(14) 0.0794(15) 0.0683(13) -0.0308(12) 0.0464(12) -0.0234(12) O118 0.0514(10) 0.0455(11) 0.0633(12) -0.0045(9) 0.0348(10) -0.0075(8) C2 0.0509(15) 0.0560(19) 0.0545(17) -0.0009(15) 0.0328(14) 0.0072(14) C3 0.0376(13) 0.0496(15) 0.0429(13) -0.0020(12) 0.0246(11) -0.0015(11) C4 0.0445(14) 0.0482(16) 0.0417(13) 0.0033(12) 0.0252(12) 0.0053(12) C5 0.0524(15) 0.0551(17) 0.0468(15) 0.0021(13) 0.0319(13) -0.0035(13) C6 0.0425(13) 0.0545(16) 0.0474(14) -0.0024(13) 0.0276(12) -0.0055(13) C7 0.0413(13) 0.0460(15) 0.0444(13) -0.0024(12) 0.0283(11) 0.0004(11) C8 0.0402(13) 0.0425(14) 0.0401(13) -0.0028(11) 0.0249(11) -0.0029(11) C9 0.0413(13) 0.0524(16) 0.0429(14) -0.0046(12) 0.0254(12) -0.0094(12) C10 0.0556(16) 0.0588(19) 0.0505(16) 0.0012(14) 0.0297(14) -0.0121(14) C11 0.0604(18) 0.087(2) 0.0530(17) 0.0105(17) 0.0328(15) -0.0192(17) C12 0.072(2) 0.105(3) 0.0584(19) -0.010(2) 0.0472(18) -0.017(2) C13 0.0630(18) 0.087(2) 0.0551(17) -0.0136(17) 0.0409(16) -0.0098(17) C14 0.0494(15) 0.0613(18) 0.0470(15) -0.0078(14) 0.0328(13) -0.0079(13) C16 0.0441(14) 0.0579(17) 0.0334(12) 0.0047(12) 0.0220(11) 0.0028(13) C19 0.0581(17) 0.0571(19) 0.0667(19) -0.0045(16) 0.0256(15) -0.0063(15) C21 0.0607(18) 0.110(3) 0.0481(16) -0.0086(18) 0.0294(15) -0.0167(19) C22 0.072(2) 0.090(3) 0.091(3) 0.028(2) 0.045(2) 0.027(2) C23 0.0404(15) 0.106(3) 0.0555(17) 0.0066(18) 0.0223(14) -0.0014(17) C102 0.0399(13) 0.0388(15) 0.0534(15) -0.0041(13) 0.0284(12) -0.0017(12) C103 0.0360(12) 0.0371(13) 0.0450(13) -0.0029(11) 0.0264(11) -0.0024(10) C104 0.0394(13) 0.0406(14) 0.0472(14) 0.0011(11) 0.0251(12) 0.0055(11) C105 0.0460(14) 0.0534(16) 0.0471(15) 0.0084(13) 0.0258(12) 0.0055(13) C106 0.0481(14) 0.0498(16) 0.0463(14) 0.0014(12) 0.0314(12) -0.0027(12) C107 0.0412(13) 0.0354(13) 0.0457(13) -0.0043(11) 0.0283(11) -0.0038(11) C108 0.0367(12) 0.0328(13) 0.0410(12) -0.0035(10) 0.0242(11) -0.0016(10) C109 0.0349(12) 0.0426(14) 0.0417(13) -0.0002(11) 0.0251(11) -0.0030(11) C110 0.0435(13) 0.0427(15) 0.0497(15) 0.0057(12) 0.0313(12) -0.0003(12) C111 0.0460(14) 0.0664(19) 0.0485(16) 0.0104(14) 0.0298(13) 0.0038(13) C112 0.0449(15) 0.074(2) 0.0418(14) -0.0028(14) 0.0224(12) -0.0068(14) C113 0.0503(15) 0.0564(18) 0.0490(15) -0.0145(14) 0.0286(13) -0.0135(14) C114 0.0395(13) 0.0417(15) 0.0482(14) -0.0034(12) 0.0270(12) -0.0041(12) C116 0.0336(12) 0.0472(15) 0.0476(15) -0.0007(13) 0.0198(12) 0.0065(11) C119 0.0463(15) 0.0468(16) 0.082(2) 0.0031(15) 0.0306(15) -0.0041(13) C121 0.0431(14) 0.0616(18) 0.0588(16) -0.0003(14) 0.0325(13) -0.0051(13) C122 0.0528(16) 0.0566(18) 0.077(2) -0.0103(15) 0.0408(16) 0.0007(14) C123 0.0527(16) 0.100(3) 0.0608(18) -0.0042(17) 0.0399(15) -0.0010(17) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2016(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Si20 . C7 . 1.878(2) yes Si20 . C21 . 1.872(3) yes Si20 . C22 . 1.871(4) yes Si20 . C23 . 1.872(3) yes Si120 . C107 . 1.886(2) yes Si120 . C121 . 1.866(3) yes Si120 . C122 . 1.873(3) yes Si120 . C123 . 1.872(3) yes O1 . C2 . 1.368(3) yes O1 . C14 . 1.394(3) yes O15 . C2 . 1.194(3) yes O17 . C16 . 1.193(3) yes O18 . C16 . 1.339(3) yes O18 . C19 . 1.443(3) yes O101 . C102 . 1.368(3) yes O101 . C114 . 1.393(3) yes O115 . C102 . 1.191(3) yes O117 . C116 . 1.195(3) yes O118 . C116 . 1.336(3) yes O118 . C119 . 1.447(3) yes C2 . C3 . 1.513(4) yes C3 . C4 . 1.541(3) yes C3 . C8 . 1.539(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.530(3) yes C4 . C16 . 1.509(4) yes C4 . H41 . 1.000 no C5 . C6 . 1.509(3) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C7 . 1.331(3) yes C6 . H61 . 1.000 no C7 . C8 . 1.539(3) yes C8 . C9 . 1.511(3) yes C8 . H81 . 1.000 no C9 . C10 . 1.381(4) yes C9 . C14 . 1.381(4) yes C10 . C11 . 1.401(4) yes C10 . H101 . 1.000 no C11 . C12 . 1.380(5) yes C11 . H111 . 1.000 no C12 . C13 . 1.369(5) yes C12 . H121 . 1.000 no C13 . C14 . 1.376(4) yes C13 . H131 . 1.000 no C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . H221 . 1.000 no C22 . H222 . 1.000 no C22 . H223 . 1.000 no C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no C102 . C103 . 1.508(3) yes C103 . C104 . 1.532(3) yes C103 . C108 . 1.540(3) yes C103 . H1031 . 1.000 no C104 . C105 . 1.536(3) yes C104 . C116 . 1.518(4) yes C104 . H1041 . 1.000 no C105 . C106 . 1.504(3) yes C105 . H1051 . 1.000 no C105 . H1052 . 1.000 no C106 . C107 . 1.339(3) yes C106 . H1061 . 1.000 no C107 . C108 . 1.534(3) yes C108 . C109 . 1.516(3) yes C108 . H1081 . 1.000 no C109 . C110 . 1.387(3) yes C109 . C114 . 1.383(3) yes C110 . C111 . 1.389(4) yes C110 . H1101 . 1.000 no C111 . C112 . 1.379(4) yes C111 . H1111 . 1.000 no C112 . C113 . 1.376(4) yes C112 . H1121 . 1.000 no C113 . C114 . 1.387(3) yes C113 . H1131 . 1.000 no C119 . H1191 . 1.000 no C119 . H1192 . 1.000 no C119 . H1193 . 1.000 no C121 . H1211 . 1.000 no C121 . H1212 . 1.000 no C121 . H1213 . 1.000 no C122 . H1221 . 1.000 no C122 . H1222 . 1.000 no C122 . H1223 . 1.000 no C123 . H1231 . 1.000 no C123 . H1232 . 1.000 no C123 . H1233 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 . Si20 . C21 . 113.12(13) yes C7 . Si20 . C22 . 109.12(14) yes C21 . Si20 . C22 . 110.07(18) yes C7 . Si20 . C23 . 109.19(12) yes C21 . Si20 . C23 . 106.65(15) yes C22 . Si20 . C23 . 108.58(17) yes C107 . Si120 . C121 . 112.70(12) yes C107 . Si120 . C122 . 107.84(12) yes C121 . Si120 . C122 . 111.66(14) yes C107 . Si120 . C123 . 109.76(12) yes C121 . Si120 . C123 . 106.55(13) yes C122 . Si120 . C123 . 108.25(15) yes C2 . O1 . C14 . 120.6(2) yes C16 . O18 . C19 . 116.2(2) yes C102 . O101 . C114 . 120.30(19) yes C116 . O118 . C119 . 115.7(2) yes O1 . C2 . O15 . 117.4(3) yes O1 . C2 . C3 . 116.6(2) yes O15 . C2 . C3 . 126.0(3) yes C2 . C3 . C4 . 110.3(2) yes C2 . C3 . C8 . 110.2(2) yes C4 . C3 . C8 . 111.53(19) yes C2 . C3 . H31 . 108.2 no C4 . C3 . H31 . 108.2 no C8 . C3 . H31 . 108.2 no C3 . C4 . C5 . 110.9(2) yes C3 . C4 . C16 . 108.1(2) yes C5 . C4 . C16 . 112.6(2) yes C3 . C4 . H41 . 108.4 no C5 . C4 . H41 . 108.4 no C16 . C4 . H41 . 108.4 no C4 . C5 . C6 . 114.0(2) yes C4 . C5 . H51 . 108.3 no C6 . C5 . H51 . 108.3 no C4 . C5 . H52 . 108.3 no C6 . C5 . H52 . 108.3 no H51 . C5 . H52 . 109.5 no C5 . C6 . C7 . 127.4(2) yes C5 . C6 . H61 . 116.3 no C7 . C6 . H61 . 116.3 no Si20 . C7 . C6 . 119.76(19) yes Si20 . C7 . C8 . 121.47(17) yes C6 . C7 . C8 . 118.6(2) yes C3 . C8 . C7 . 110.0(2) yes C3 . C8 . C9 . 106.47(19) yes C7 . C8 . C9 . 113.75(19) yes C3 . C8 . H81 . 108.8 no C7 . C8 . H81 . 108.8 no C9 . C8 . H81 . 108.8 no C8 . C9 . C10 . 123.8(2) yes C8 . C9 . C14 . 118.3(2) yes C10 . C9 . C14 . 117.9(2) yes C9 . C10 . C11 . 119.9(3) yes C9 . C10 . H101 . 120.1 no C11 . C10 . H101 . 120.0 no C10 . C11 . C12 . 120.5(3) yes C10 . C11 . H111 . 119.8 no C12 . C11 . H111 . 119.8 no C11 . C12 . C13 . 119.8(3) yes C11 . C12 . H121 . 120.1 no C13 . C12 . H121 . 120.1 no C12 . C13 . C14 . 119.1(3) yes C12 . C13 . H131 . 120.4 no C14 . C13 . H131 . 120.4 no O1 . C14 . C9 . 121.0(2) yes O1 . C14 . C13 . 116.2(3) yes C9 . C14 . C13 . 122.7(3) yes C4 . C16 . O18 . 110.4(2) yes C4 . C16 . O17 . 126.3(2) yes O18 . C16 . O17 . 123.3(3) yes O18 . C19 . H191 . 109.5 no O18 . C19 . H192 . 109.5 no H191 . C19 . H192 . 109.5 no O18 . C19 . H193 . 109.5 no H191 . C19 . H193 . 109.5 no H192 . C19 . H193 . 109.5 no Si20 . C21 . H211 . 109.5 no Si20 . C21 . H212 . 109.5 no H211 . C21 . H212 . 109.5 no Si20 . C21 . H213 . 109.5 no H211 . C21 . H213 . 109.5 no H212 . C21 . H213 . 109.5 no Si20 . C22 . H221 . 109.5 no Si20 . C22 . H222 . 109.5 no H221 . C22 . H222 . 109.5 no Si20 . C22 . H223 . 109.5 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no Si20 . C23 . H231 . 109.5 no Si20 . C23 . H232 . 109.5 no H231 . C23 . H232 . 109.5 no Si20 . C23 . H233 . 109.5 no H231 . C23 . H233 . 109.5 no H232 . C23 . H233 . 109.5 no O101 . C102 . O115 . 116.9(2) yes O101 . C102 . C103 . 116.9(2) yes O115 . C102 . C103 . 126.2(2) yes C102 . C103 . C104 . 109.4(2) yes C102 . C103 . C108 . 110.42(18) yes C104 . C103 . C108 . 111.66(19) yes C102 . C103 . H1031 . 108.4 no C104 . C103 . H1031 . 108.4 no C108 . C103 . H1031 . 108.4 no C103 . C104 . C105 . 110.09(19) yes C103 . C104 . C116 . 111.6(2) yes C105 . C104 . C116 . 111.8(2) yes C103 . C104 . H1041 . 107.7 no C105 . C104 . H1041 . 107.7 no C116 . C104 . H1041 . 107.7 no C104 . C105 . C106 . 113.3(2) yes C104 . C105 . H1051 . 108.5 no C106 . C105 . H1051 . 108.5 no C104 . C105 . H1052 . 108.5 no C106 . C105 . H1052 . 108.5 no H1051 . C105 . H1052 . 109.5 no C105 . C106 . C107 . 127.3(2) yes C105 . C106 . H1061 . 116.3 no C107 . C106 . H1061 . 116.3 no Si120 . C107 . C106 . 118.64(19) yes Si120 . C107 . C108 . 122.27(17) yes C106 . C107 . C108 . 118.8(2) yes C103 . C108 . C107 . 110.90(19) yes C103 . C108 . C109 . 106.66(18) yes C107 . C108 . C109 . 114.05(18) yes C103 . C108 . H1081 . 108.4 no C107 . C108 . H1081 . 108.4 no C109 . C108 . H1081 . 108.4 no C108 . C109 . C110 . 124.3(2) yes C108 . C109 . C114 . 118.3(2) yes C110 . C109 . C114 . 117.4(2) yes C109 . C110 . C111 . 120.7(2) yes C109 . C110 . H1101 . 119.7 no C111 . C110 . H1101 . 119.7 no C110 . C111 . C112 . 120.6(3) yes C110 . C111 . H1111 . 119.7 no C112 . C111 . H1111 . 119.7 no C111 . C112 . C113 . 119.8(2) yes C111 . C112 . H1121 . 120.1 no C113 . C112 . H1121 . 120.1 no C112 . C113 . C114 . 119.0(3) yes C112 . C113 . H1131 . 120.5 no C114 . C113 . H1131 . 120.5 no O101 . C114 . C113 . 116.1(2) yes O101 . C114 . C109 . 121.4(2) yes C113 . C114 . C109 . 122.5(2) yes C104 . C116 . O118 . 110.8(2) yes C104 . C116 . O117 . 125.7(3) yes O118 . C116 . O117 . 123.5(3) yes O118 . C119 . H1191 . 109.5 no O118 . C119 . H1192 . 109.5 no H1191 . C119 . H1192 . 109.5 no O118 . C119 . H1193 . 109.5 no H1191 . C119 . H1193 . 109.5 no H1192 . C119 . H1193 . 109.5 no Si120 . C121 . H1211 . 109.5 no Si120 . C121 . H1212 . 109.5 no H1211 . C121 . H1212 . 109.5 no Si120 . C121 . H1213 . 109.5 no H1211 . C121 . H1213 . 109.5 no H1212 . C121 . H1213 . 109.5 no Si120 . C122 . H1221 . 109.5 no Si120 . C122 . H1222 . 109.5 no H1221 . C122 . H1222 . 109.5 no Si120 . C122 . H1223 . 109.5 no H1221 . C122 . H1223 . 109.5 no H1222 . C122 . H1223 . 109.5 no Si120 . C123 . H1231 . 109.5 no Si120 . C123 . H1232 . 109.5 no H1231 . C123 . H1232 . 109.5 no Si120 . C123 . H1233 . 109.5 no H1231 . C123 . H1233 . 109.5 no H1232 . C123 . H1233 . 109.5 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C10 3.339(4) . 1_565 no O15 C19 3.436(4) . 1_565 no O17 C102 2.923(5) . 1_545 no O17 C103 3.193(5) . 1_545 no O17 O101 3.222(4) . 1_545 no O17 O115 3.233(4) . 1_545 no O101 C110 3.379(3) . 1_565 no O115 C119 3.172(4) . 1_565 no O115 O118 3.313(3) . 1_565 no O115 C108 3.424(3) . 1_565 no O115 C116 3.537(3) . 1_565 no O117 C12 3.507(6) . 6_564 no O117 C119 3.555(3) . 2_565 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag SI20 C7 C6 C5 . . . . 176.2(2) no SI20 C7 C8 C3 . . . . 156.8(2) no SI20 C7 C8 C9 . . . . 37.5(3) no SI120 C107 C106 C105 . . . . 170.9(2) no SI120 C107 C108 C103 . . . . 164.5(2) no SI120 C107 C108 C109 . . . . 44.1(3) no O1 C2 C3 C4 . . . . -163.9(3) no O1 C2 C3 C8 . . . . -40.2(4) no O1 C14 C9 C8 . . . . -0.4(3) no O1 C14 C9 C10 . . . . -178.6(2) no O1 C14 C13 C12 . . . . 179.5(2) no O15 C2 O1 C14 . . . . 179.2(3) no O15 C2 C3 C4 . . . . 16.8(4) no O15 C2 C3 C8 . . . . 140.5(3) no O17 C16 O18 C19 . . . . 1.1(5) no O17 C16 C4 C3 . . . . -105.6(4) no O17 C16 C4 C5 . . . . 17.3(4) no O18 C16 C4 C3 . . . . 72.9(3) no O18 C16 C4 C5 . . . . -164.3(2) no O101 C102 C103 C104 . . . . -164.4(3) no O101 C102 C103 C108 . . . . -41.1(4) no O101 C114 C109 C108 . . . . -1.9(5) no O101 C114 C109 C110 . . . . 179.1(3) no O101 C114 C113 C112 . . . . -177.4(3) no O115 C102 O101 C114 . . . . -179.1(3) no O115 C102 C103 C104 . . . . 15.9(5) no O115 C102 C103 C108 . . . . 139.2(4) no O117 C116 O118 C119 . . . . 1.3(3) no O117 C116 C104 C103 . . . . -130.0(3) no O117 C116 C104 C105 . . . . -6.3(3) no O118 C116 C104 C103 . . . . 52.8(3) no O118 C116 C104 C105 . . . . 176.5(2) no C2 O1 C14 C9 . . . . 22.4(4) no C2 O1 C14 C13 . . . . -158.9(3) no C2 C3 C4 C5 . . . . 65.3(3) no C2 C3 C4 C16 . . . . -170.8(2) no C2 C3 C8 C7 . . . . -67.0(4) no C2 C3 C8 C9 . . . . 56.7(3) no C3 C2 O1 C14 . . . . -0.1(4) no C3 C4 C5 C6 . . . . 29.5(3) no C3 C8 C7 C6 . . . . -27.5(4) no C3 C8 C9 C10 . . . . 139.7(2) no C3 C8 C9 C14 . . . . -38.3(3) no C4 C3 C8 C7 . . . . 56.0(3) no C4 C3 C8 C9 . . . . 179.7(2) no C4 C5 C6 C7 . . . . -1.4(5) no C4 C16 O18 C19 . . . . -177.4(3) no C5 C4 C3 C8 . . . . -57.6(3) no C5 C6 C7 C8 . . . . 0.4(5) no C6 C5 C4 C16 . . . . -91.8(3) no C6 C7 SI20 C21 . . . . 117.8(3) no C6 C7 SI20 C22 . . . . -119.3(3) no C6 C7 SI20 C23 . . . . -0.8(3) no C6 C7 C8 C9 . . . . -146.8(3) no C7 C8 C9 C10 . . . . -98.9(3) no C7 C8 C9 C14 . . . . 83.0(3) no C8 C3 C4 C16 . . . . 66.3(3) no C8 C7 SI20 C21 . . . . -66.6(3) no C8 C7 SI20 C22 . . . . 56.3(3) no C8 C7 SI20 C23 . . . . 174.9(2) no C8 C9 C10 C11 . . . . -179.8(2) no C8 C9 C14 C13 . . . . -179.0(2) no C9 C10 C11 C12 . . . . -0.2(4) no C9 C14 C13 C12 . . . . -1.8(4) no C10 C9 C14 C13 . . . . 2.8(4) no C10 C11 C12 C13 . . . . 1.3(4) no C11 C10 C9 C14 . . . . -1.8(4) no C11 C12 C13 C14 . . . . -0.3(4) no C102 O101 C114 C109 . . . . 22.2(5) no C102 O101 C114 C113 . . . . -159.2(3) no C102 C103 C104 C105 . . . . 62.6(3) no C102 C103 C104 C116 . . . . -172.8(3) no C102 C103 C108 C107 . . . . -68.7(3) no C102 C103 C108 C109 . . . . 56.1(3) no C103 C102 O101 C114 . . . . 1.2(5) no C103 C104 C105 C106 . . . . 34.1(3) no C103 C108 C107 C106 . . . . -21.6(3) no C103 C108 C109 C110 . . . . 142.4(3) no C103 C108 C109 C114 . . . . -36.5(4) no C104 C103 C108 C107 . . . . 53.3(3) no C104 C103 C108 C109 . . . . 178.0(2) no C104 C105 C106 C107 . . . . -3.4(4) no C104 C116 O118 C119 . . . . 178.6(2) no C105 C104 C103 C108 . . . . -59.9(3) no C105 C106 C107 C108 . . . . -3.2(4) no C106 C105 C104 C116 . . . . -90.4(2) no C106 C107 SI120 C121 . . . . 121.2(2) no C106 C107 SI120 C122 . . . . -115.1(2) no C106 C107 SI120 C123 . . . . 2.6(3) no C106 C107 C108 C109 . . . . -142.1(2) no C107 C108 C109 C110 . . . . -94.8(4) no C107 C108 C109 C114 . . . . 86.3(4) no C108 C103 C104 C116 . . . . 64.7(4) no C108 C107 SI120 C121 . . . . -64.9(2) no C108 C107 SI120 C122 . . . . 58.8(2) no C108 C107 SI120 C123 . . . . 176.5(2) no C108 C109 C110 C111 . . . . 179.1(3) no C108 C109 C114 C113 . . . . 179.7(3) no C109 C110 C111 C112 . . . . 1.5(6) no C109 C114 C113 C112 . . . . 1.2(6) no C110 C109 C114 C113 . . . . 0.7(5) no C110 C111 C112 C113 . . . . 0.4(6) no C111 C110 C109 C114 . . . . -2.0(5) no C111 C112 C113 C114 . . . . -1.7(6) no #------------------------------------------------------------------------------ #===END data_mss04A # # 1. SUBMISSION DETAILS _publ_requested_journal Org.Biomol.Chem. _publ_contact_author_name ' Michael S. Sherburn ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_author_email 'sherburn@rsc.anu.edu.au ' _publ_contact_author_phone ' 61 2 6125 4988 ' _publ_contact_author_fax ' 61 2 6125 8114 ' loop_ _publ_author_name _publ_author_address 'Pearson, Emma L.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Willis, Anthony C.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Sherburn, Michael S.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Paddon-Row, Michael N.' ; School of Chemistry, University of New South Wales, Sydney, N. S. W. 2052, Australia ; _audit_creation_date 04-15-11 _audit_creation_method CRYSTALS_ver_12-03-99 # 11121011 mss04A _audit_update_record ; 2004-11-15 - Report on C15 H13 Br O4 by Anthony C. Willis for Craig Turner and Mick Sherburn 2004-11-15 - passes checkcif tests with minor warnings ; _publ_requested_category ' fo ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Controlling cis/trans-selectivity in intramolecular Diels--Alder reactions of benzo-tethered, ester linked 1,3,9-decatrienes ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~15~H~13~BrO~4~ is reported. ; _publ_section_comment #Text of the paper ; The crystallographic asymmetric unit consists of one C~15~H~13~BrO~4~ molecule. There were no outstanding features in the final difference electron density map. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; Hydrogen atoms were included at calculated positions and during refinement they ride on the atom to which they are attached. ; _publ_section_exptl_prep ; The compound was prepared by CIT and recrystallized from ethylacetate/heptane. The sample ID is CTM026. ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; #============================================================= _cell_length_a 9.3080(2) _cell_angle_alpha 90 _cell_length_b 10.1060(2) _cell_angle_beta 95.7272(12) _cell_length_c 14.4185(3) _cell_angle_gamma 90 _cell_volume 1349.53(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'Br ' -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C15 H13 Br O4 ' _chemical_formula_moiety ' C15 H13 Br O4 ' _chemical_compound_source ; ? ; _chemical_formula_weight 337.17 _cell_measurement_reflns_used 15962 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 200 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.11 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.056 _diffrn_measurement_device_type ; Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 2.0 deg at rate 40 sec/frame, crystal-detector distance 28mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more. ; # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.070 0 0 1 0.080 0 0 -1 0.030 5 5 0 0.120 1 -2 0 0.100 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.483 _exptl_absorpt_correction_T_max 0.733 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.040 # Sheldrick geometric definitions 0.47 0.71 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 200 _diffrn_reflns_number 29685 _reflns_number_total 3094 _diffrn_reflns_av_R_equivalents 0.04 # Number of reflections with Friedels Law is 3094 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3099 _diffrn_reflns_theta_min 2.840 _diffrn_reflns_theta_max 27.496 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.496 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _refine_diff_density_min -0.34 _refine_diff_density_max 0.29 _refine_ls_number_reflns 1922 _refine_ls_number_restraints 0 _refine_ls_number_parameters 182 #_refine_ls_R_factor_ref 0.0208 _refine_ls_wR_factor_ref 0.0233 _refine_ls_goodness_of_fit_ref 1.1202 #_reflns_number_all 2390 _refine_ls_R_factor_all 0.0266 _refine_ls_wR_factor_all 0.0264 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 1922 _refine_ls_R_factor_gt 0.0208 _refine_ls_wR_factor_gt 0.0233 _refine_ls_shift/su_max 0.000511 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.409 0.111 0.188 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Altomare, A., Cascarano, G., Giacovazzo C., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Larson, A.C. (1970). The Inclusion of Secondary Extinction in Least-Squares Refinement in Crystal Structures. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 291-294 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Br1 Br 0.57860(2) 0.03658(2) 0.376508(17) 0.0389 1.0000 Uani . . . . . . O1 O 0.01126(16) 0.00000(15) 0.37385(12) 0.0395 1.0000 Uani . . . . . . O2 O -0.12040(17) 0.16679(18) 0.41106(14) 0.0508 1.0000 Uani . . . . . . O3 O 0.2928(3) 0.3336(2) 0.59670(14) 0.0696 1.0000 Uani . . . . . . O4 O 0.2512(2) 0.52012(18) 0.51890(14) 0.0555 1.0000 Uani . . . . . . C1 C 0.2687(2) 0.2474(2) 0.32140(15) 0.0348 1.0000 Uani . . . . . . C2 C 0.2674(2) 0.1590(2) 0.40536(14) 0.0279 1.0000 Uani . . . . . . C3 C 0.2722(2) 0.0149(2) 0.37823(14) 0.0295 1.0000 Uani . . . . . . C4 C 0.3987(2) -0.0531(2) 0.36396(14) 0.0334 1.0000 Uani . . . . . . C5 C 0.3989(3) -0.1861(2) 0.34030(16) 0.0413 1.0000 Uani . . . . . . C6 C 0.2684(3) -0.2547(2) 0.32954(18) 0.0440 1.0000 Uani . . . . . . C7 C 0.1411(3) -0.1910(2) 0.34243(16) 0.0410 1.0000 Uani . . . . . . C8 C 0.1459(2) -0.0578(2) 0.36611(15) 0.0339 1.0000 Uani . . . . . . C9 C -0.0008(2) 0.1221(2) 0.41249(15) 0.0351 1.0000 Uani . . . . . . C10 C 0.1345(2) 0.1862(2) 0.45764(14) 0.0299 1.0000 Uani . . . . . . C11 C 0.1081(2) 0.3354(2) 0.46853(15) 0.0331 1.0000 Uani . . . . . . C12 C 0.0841(2) 0.4037(2) 0.37346(16) 0.0368 1.0000 Uani . . . . . . C13 C 0.1873(2) 0.3554(2) 0.30758(16) 0.0373 1.0000 Uani . . . . . . C14 C 0.2281(2) 0.3937(2) 0.53428(16) 0.0357 1.0000 Uani . . . . . . C15 C 0.3589(4) 0.5857(3) 0.5822(3) 0.0709 1.0000 Uani . . . . . . H11 H 0.3346 0.2238 0.27326 0.0421 1.0000 Uiso R . . . . . H21 H 0.3556 0.1787 0.44859 0.0335 1.0000 Uiso R . . . . . H51 H 0.4915 -0.2323 0.33152 0.0501 1.0000 Uiso R . . . . . H61 H 0.2672 -0.3507 0.31256 0.0532 1.0000 Uiso R . . . . . H71 H 0.0469 -0.2391 0.33351 0.0489 1.0000 Uiso R . . . . . H101 H 0.1541 0.1479 0.52161 0.0361 1.0000 Uiso R . . . . . H111 H 0.0168 0.3452 0.49903 0.0399 1.0000 Uiso R . . . . . H121 H 0.0976 0.5012 0.38245 0.0439 1.0000 Uiso R . . . . . H122 H -0.0168 0.3855 0.34574 0.0439 1.0000 Uiso R . . . . . H131 H 0.1947 0.4069 0.24905 0.0446 1.0000 Uiso R . . . . . H151 H 0.3690 0.6796 0.5619 0.0829 1.0000 Uiso R . . . . . H152 H 0.3279 0.5836 0.6466 0.0829 1.0000 Uiso R . . . . . H153 H 0.4534 0.5389 0.5814 0.0829 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03085(11) 0.04044(13) 0.04629(13) -0.00379(12) 0.00880(8) -0.00095(11) O1 0.0298(8) 0.0365(9) 0.0517(10) -0.0050(7) 0.0022(7) -0.0089(6) O2 0.0272(8) 0.0483(10) 0.0774(13) -0.0049(9) 0.0076(8) -0.0043(8) O3 0.0922(16) 0.0500(11) 0.0584(12) 0.0016(10) -0.0330(11) -0.0035(11) O4 0.0622(11) 0.0344(9) 0.0654(12) -0.0033(8) -0.0166(9) -0.0096(9) C1 0.0339(11) 0.0373(12) 0.0341(11) 0.0007(9) 0.0084(9) -0.0073(9) C2 0.0254(9) 0.0277(10) 0.0306(10) -0.0013(8) 0.0035(8) -0.0036(8) C3 0.0320(10) 0.0303(10) 0.0265(9) -0.0006(8) 0.0038(7) -0.0041(8) C4 0.0367(10) 0.0347(11) 0.0291(10) -0.0012(9) 0.0058(8) -0.0027(9) C5 0.0490(14) 0.0370(12) 0.0393(12) -0.0039(10) 0.0107(10) 0.0023(11) C6 0.0570(15) 0.0292(11) 0.0467(14) -0.0034(10) 0.0090(12) -0.0046(11) C7 0.0482(14) 0.0340(12) 0.0402(13) -0.0023(10) 0.0014(10) -0.0116(10) C8 0.0348(10) 0.0349(12) 0.0319(11) -0.0004(9) 0.0024(8) -0.0057(9) C9 0.0319(11) 0.0348(11) 0.0390(12) 0.0030(9) 0.0058(9) -0.0066(9) C10 0.0288(10) 0.0300(10) 0.0314(11) 0.0013(8) 0.0058(8) -0.0032(8) C11 0.0300(10) 0.0323(11) 0.0374(11) 0.0003(9) 0.0058(8) 0.0006(9) C12 0.0359(11) 0.0325(10) 0.0414(12) 0.0029(11) 0.0004(9) -0.0001(10) C13 0.0390(12) 0.0368(12) 0.0358(11) 0.0066(9) 0.0024(9) -0.0057(9) C14 0.0367(11) 0.0340(12) 0.0367(12) -0.0054(10) 0.0045(9) 0.0029(10) C15 0.072(2) 0.0497(17) 0.085(2) -0.0205(16) -0.0192(18) -0.0145(15) _refine_ls_extinction_coef 57(4) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 . C4 . 1.897(2) yes O1 . C8 . 1.398(3) yes O1 . C9 . 1.363(3) yes O2 . C9 . 1.200(3) yes O3 . C14 . 1.197(3) yes O4 . C14 . 1.318(3) yes O4 . C15 . 1.447(3) yes C1 . C2 . 1.506(3) yes C1 . C13 . 1.332(3) yes C1 . H11 . 1.000 no C2 . C3 . 1.509(3) yes C2 . C10 . 1.537(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.396(3) yes C3 . C8 . 1.383(3) yes C4 . C5 . 1.386(3) yes C5 . C6 . 1.394(3) yes C5 . H51 . 1.000 no C6 . C7 . 1.377(4) yes C6 . H61 . 1.000 no C7 . C8 . 1.388(3) yes C7 . H71 . 1.000 no C9 . C10 . 1.505(3) yes C10 . C11 . 1.538(3) yes C10 . H101 . 1.000 no C11 . C12 . 1.531(3) yes C11 . C14 . 1.511(3) yes C11 . H111 . 1.000 no C12 . C13 . 1.499(3) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C13 . H131 . 1.000 no C15 . H151 . 1.000 no C15 . H152 . 1.000 no C15 . H153 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C8 . O1 . C9 . 121.48(16) yes C14 . O4 . C15 . 116.9(2) yes C2 . C1 . C13 . 123.8(2) yes C2 . C1 . H11 . 118.100 no C13 . C1 . H11 . 118.100 no C1 . C2 . C3 . 111.18(17) yes C1 . C2 . C10 . 111.08(17) yes C3 . C2 . C10 . 110.23(16) yes C1 . C2 . H21 . 108.096 no C3 . C2 . H21 . 108.082 no C10 . C2 . H21 . 108.047 no C2 . C3 . C4 . 124.11(18) yes C2 . C3 . C8 . 119.93(19) yes C4 . C3 . C8 . 116.0(2) yes Br1 . C4 . C3 . 119.97(16) yes Br1 . C4 . C5 . 117.64(17) yes C3 . C4 . C5 . 122.4(2) yes C4 . C5 . C6 . 119.2(2) yes C4 . C5 . H51 . 120.402 no C6 . C5 . H51 . 120.443 no C5 . C6 . C7 . 120.3(2) yes C5 . C6 . H61 . 119.849 no C7 . C6 . H61 . 119.876 no C6 . C7 . C8 . 118.6(2) yes C6 . C7 . H71 . 120.687 no C8 . C7 . H71 . 120.670 no O1 . C8 . C7 . 114.69(19) yes O1 . C8 . C3 . 121.70(19) yes C7 . C8 . C3 . 123.6(2) yes O1 . C9 . O2 . 116.6(2) yes O1 . C9 . C10 . 117.85(19) yes O2 . C9 . C10 . 125.4(2) yes C2 . C10 . C9 . 113.00(17) yes C2 . C10 . C11 . 111.71(16) yes C9 . C10 . C11 . 109.33(17) yes C2 . C10 . H101 . 107.541 no C9 . C10 . H101 . 107.492 no C11 . C10 . H101 . 107.517 no C10 . C11 . C12 . 111.16(18) yes C10 . C11 . C14 . 109.32(18) yes C12 . C11 . C14 . 114.76(19) yes C10 . C11 . H111 . 107.054 no C12 . C11 . H111 . 107.118 no C14 . C11 . H111 . 107.043 no C11 . C12 . C13 . 112.02(19) yes C11 . C12 . H121 . 108.823 no C13 . C12 . H121 . 108.831 no C11 . C12 . H122 . 108.813 no C13 . C12 . H122 . 108.817 no H121 . C12 . H122 . 109.508 no C12 . C13 . C1 . 124.3(2) yes C12 . C13 . H131 . 117.875 no C1 . C13 . H131 . 117.839 no C11 . C14 . O4 . 113.3(2) yes C11 . C14 . O3 . 124.0(2) yes O4 . C14 . O3 . 122.7(2) yes O4 . C15 . H151 . 109.289 no O4 . C15 . H152 . 109.271 no H151 . C15 . H152 . 109.652 no O4 . C15 . H153 . 109.316 no H151 . C15 . H153 . 109.651 no H152 . C15 . H153 . 109.647 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Br1 O2 3.090(2) . 1_655 no O1 C9 3.329(3) . 2_556 no O1 C13 3.381(3) . 3_545 no O1 C10 3.456(3) . 2_556 no O1 O2 3.586(2) . 2_556 no O2 C15 3.352(4) . 2_566 no O2 C8 3.427(3) . 2_556 no O2 O4 3.572(3) . 2_566 no O2 C7 3.587(3) . 2_556 no O3 C5 3.280(4) . 2_656 no O3 C1 3.371(3) . 4 no O4 C6 3.570(3) . 1_565 no C7 C13 3.595(3) . 3_545 no C9 C9 3.529(4) . 2_556 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Br1 C4 C3 C2 . . . . -1.1(3) no Br1 C4 C3 C8 . . . . 179.0(2) no Br1 C4 C5 C6 . . . . -179.3(2) no O1 C8 C3 C2 . . . . 3.2(3) no O1 C8 C3 C4 . . . . -176.9(2) no O1 C8 C7 C6 . . . . 177.4(2) no O1 C9 C10 C2 . . . . 37.2(3) no O1 C9 C10 C11 . . . . 162.3(2) no O2 C9 O1 C8 . . . . 175.7(2) no O2 C9 C10 C2 . . . . -146.3(2) no O2 C9 C10 C11 . . . . -21.2(3) no O3 C14 O4 C15 . . . . -0.7(4) no O3 C14 C11 C10 . . . . -29.8(3) no O3 C14 C11 C12 . . . . -155.5(2) no O4 C14 C11 C10 . . . . 152.9(2) no O4 C14 C11 C12 . . . . 27.3(3) no C1 C2 C3 C4 . . . . 82.3(2) no C1 C2 C3 C8 . . . . -97.7(2) no C1 C2 C10 C9 . . . . 79.3(2) no C1 C2 C10 C11 . . . . -44.5(2) no C1 C13 C12 C11 . . . . 13.6(3) no C2 C1 C13 C12 . . . . 0.2(3) no C2 C3 C4 C5 . . . . 179.1(2) no C2 C3 C8 C7 . . . . -179.1(2) no C2 C10 C11 C12 . . . . 59.5(2) no C2 C10 C11 C14 . . . . -68.2(2) no C3 C2 C1 C13 . . . . 138.6(2) no C3 C2 C10 C9 . . . . -44.4(2) no C3 C2 C10 C11 . . . . -168.2(2) no C3 C4 C5 C6 . . . . 0.5(3) no C3 C8 O1 C9 . . . . -14.0(3) no C3 C8 C7 C6 . . . . -0.5(3) no C4 C3 C2 C10 . . . . -154.0(2) no C4 C3 C8 C7 . . . . 0.9(3) no C4 C5 C6 C7 . . . . -0.1(4) no C5 C4 C3 C8 . . . . -0.9(3) no C5 C6 C7 C8 . . . . 0.1(4) no C7 C8 O1 C9 . . . . 168.1(2) no C8 O1 C9 C10 . . . . -7.5(3) no C8 C3 C2 C10 . . . . 25.9(3) no C9 C10 C11 C12 . . . . -66.3(2) no C9 C10 C11 C14 . . . . 166.0(2) no C10 C2 C1 C13 . . . . 15.5(3) no C10 C11 C12 C13 . . . . -42.4(2) no C11 C14 O4 C15 . . . . 176.6(2) no C13 C12 C11 C14 . . . . 82.3(2) no #------------------------------------------------------------------------------ #===END data_she0504 # # 1. SUBMISSION DETAILS _publ_requested_journal Org.Biomol.Chem. _publ_contact_author_name ' Michael S. Sherburn ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_author_email 'sherburn@rsc.anu.edu.au ' _publ_contact_author_phone ' 61 2 6125 4988 ' _publ_contact_author_fax ' 61 2 6125 8114 ' loop_ _publ_author_name _publ_author_address 'Pearson, Emma L.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Willis, Anthony C.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Sherburn, Michael S.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Paddon-Row, Michael N.' ; School of Chemistry, University of New South Wales, Sydney, N. S. W. 2052, Australia ; _audit_creation_date 05-24-01 _audit_creation_method CRYSTALS_ver_12-03-99 # 1241222 she0504 _audit_update_record ; 2005-01-24 - Report on C18 H22 O4 Si by Anthony C. Willis for Craig Turner and Mick Sherburn 2005-01-24 - passes checkcif tests with minor warnings ; _publ_requested_category ' fo ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Controlling cis/trans-selectivity in intramolecular Diels--Alder reactions of benzo-tethered, ester linked 1,3,9-decatrienes ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~18~H~22~O~4~Si is reported. ; _publ_section_comment #Text of the paper ; The crystallographic asymmetric unit consists of one C~18~H~22~O~4~Si molecule. There were no outstanding features in the final difference electron density map. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; Hydrogen atoms were included at calculated positions and during refinement they ride on the atom to which they are attached. ; _publ_section_exptl_prep ; The compound was prepared by CIT and recrystallized from ethylacetate/heptane. The sample ID is CTM050. ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; #============================================================= _cell_length_a 9.3794(2) _cell_angle_alpha 86.4869(12) _cell_length_b 9.9026(2) _cell_angle_beta 66.0202(13) _cell_length_c 10.4159(2) _cell_angle_gamma 79.5571(15) _cell_volume 869.21(3) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'Si ' 0.0817 0.0704 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937 1.1407 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C18 H22 O4 Si ' _chemical_formula_moiety ' C18 H22 O4 Si ' _chemical_compound_source ; ? ; _chemical_formula_weight 330.46 _cell_measurement_reflns_used 12376 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 200 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.152 _diffrn_measurement_device_type ; Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 2.0 deg at rate 80 sec/frame, crystal-detector distance 28mm, multiple scan sets so over 95 percent of data collected with 2-fold redundancy or more. ; # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.200 -1 0 0 0.200 0 1 0 0.150 0 -1 0 0.180 0 0 1 0.020 0 0 -1 0.070 -1 -1 0 0.200 1 1 0 0.220 0 1 -1 0.110 0 -1 1 0.100 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.951 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.042 # Sheldrick geometric definitions 0.96 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 200 _diffrn_reflns_number 19510 _reflns_number_total 3968 _diffrn_reflns_av_R_equivalents 0.04 # Number of reflections with Friedels Law is 3968 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3986 _diffrn_reflns_theta_min 2.910 _diffrn_reflns_theta_max 27.5 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.480 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -10 _reflns_limit_h_max 12 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _refine_diff_density_min -0.21 _refine_diff_density_max 0.24 _refine_ls_number_reflns 3031 _refine_ls_number_restraints 0 _refine_ls_number_parameters 209 #_refine_ls_R_factor_ref 0.0353 _refine_ls_wR_factor_ref 0.0371 _refine_ls_goodness_of_fit_ref 1.0878 #_reflns_number_all 3960 _refine_ls_R_factor_all 0.0462 _refine_ls_wR_factor_all 0.0392 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3031 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_gt 0.0371 _refine_ls_shift/su_max 0.000272 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.67 -0.466 1.78 -0.215 0.525 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Altomare, A., Cascarano, G., Giacovazzo C., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Larson, A.C. (1970). The Inclusion of Secondary Extinction in Least-Squares Refinement in Crystal Structures. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 291-294 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Si1 Si 0.16174(4) 0.84649(4) 0.66448(4) 0.0321 1.0000 Uani . . . . . . O1 O 0.75479(10) 0.62449(11) 0.32950(10) 0.0372 1.0000 Uani . . . . . . O2 O 0.81540(13) 0.55551(16) 0.11528(13) 0.0627 1.0000 Uani . . . . . . O3 O 0.28955(14) 0.82402(13) 0.10233(15) 0.0590 1.0000 Uani . . . . . . O4 O 0.29091(12) 0.60558(11) 0.16453(13) 0.0464 1.0000 Uani . . . . . . C1 C 0.52022(17) 0.89830(14) 0.28491(15) 0.0345 1.0000 Uani . . . . . . C2 C 0.45886(14) 0.76811(12) 0.35097(12) 0.0259 1.0000 Uani . . . . . . C3 C 0.48898(14) 0.73374(12) 0.48225(13) 0.0254 1.0000 Uani . . . . . . C4 C 0.37640(15) 0.76820(12) 0.61989(13) 0.0273 1.0000 Uani . . . . . . C5 C 0.42700(17) 0.74017(13) 0.72994(14) 0.0326 1.0000 Uani . . . . . . C6 C 0.58203(18) 0.68070(14) 0.70578(15) 0.0366 1.0000 Uani . . . . . . C7 C 0.68965(16) 0.64149(14) 0.57148(15) 0.0344 1.0000 Uani . . . . . . C8 C 0.64036(15) 0.66696(13) 0.46250(14) 0.0292 1.0000 Uani . . . . . . C9 C 0.71283(15) 0.60601(16) 0.22112(15) 0.0368 1.0000 Uani . . . . . . C10 C 0.54025(14) 0.64881(13) 0.24528(13) 0.0275 1.0000 Uani . . . . . . C11 C 0.53016(15) 0.68689(14) 0.10291(13) 0.0321 1.0000 Uani . . . . . . C12 C 0.61372(19) 0.80929(17) 0.03885(15) 0.0424 1.0000 Uani . . . . . . C13 C 0.59041(19) 0.91364(16) 0.14729(16) 0.0414 1.0000 Uani . . . . . . C14 C 0.35761(15) 0.71672(14) 0.12290(13) 0.0308 1.0000 Uani . . . . . . C15 C 0.12583(18) 0.61876(18) 0.1872(2) 0.0489 1.0000 Uani . . . . . . C16 C 0.1464(2) 1.01729(16) 0.5808(2) 0.0514 1.0000 Uani . . . . . . C17 C 0.06427(18) 0.72614(16) 0.60904(18) 0.0423 1.0000 Uani . . . . . . C18 C 0.0566(2) 0.8697(2) 0.85813(19) 0.0628 1.0000 Uani . . . . . . H11 H 0.50705 0.97587 0.34810 0.0447 1.0000 Uiso R . . . . . H21 H 0.34195 0.78352 0.37754 0.0319 1.0000 Uiso R . . . . . H51 H 0.34931 0.76366 0.82858 0.0407 1.0000 Uiso R . . . . . H61 H 0.61557 0.66633 0.78599 0.0490 1.0000 Uiso R . . . . . H71 H 0.80041 0.59585 0.55336 0.0449 1.0000 Uiso R . . . . . H101 H 0.48311 0.57025 0.28652 0.0334 1.0000 Uiso R . . . . . H111 H 0.58568 0.60772 0.03561 0.0389 1.0000 Uiso R . . . . . H121 H 0.72973 0.77462 -0.01164 0.0519 1.0000 Uiso R . . . . . H122 H 0.57072 0.85470 -0.02949 0.0519 1.0000 Uiso R . . . . . H131 H 0.63097 1.00146 0.11301 0.0538 1.0000 Uiso R . . . . . H151 H 0.08953 0.52873 0.2180 0.0614 1.0000 Uiso R . . . . . H152 H 0.06034 0.69027 0.2614 0.0614 1.0000 Uiso R . . . . . H153 H 0.11382 0.64636 0.0976 0.0614 1.0000 Uiso R . . . . . H161 H 0.0323 1.05675 0.6056 0.0625 1.0000 Uiso R . . . . . H162 H 0.1955 1.08042 0.6155 0.0625 1.0000 Uiso R . . . . . H163 H 0.2032 1.00632 0.4765 0.0625 1.0000 Uiso R . . . . . H171 H -0.04899 0.76779 0.63273 0.0528 1.0000 Uiso R . . . . . H172 H 0.06943 0.63730 0.65939 0.0528 1.0000 Uiso R . . . . . H173 H 0.12027 0.70900 0.50536 0.0528 1.0000 Uiso R . . . . . H181 H -0.0569 0.9110 0.88257 0.0720 1.0000 Uiso R . . . . . H182 H 0.1075 0.9321 0.89173 0.0720 1.0000 Uiso R . . . . . H183 H 0.0627 0.7786 0.90431 0.0720 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si1 0.02846(19) 0.0323(2) 0.0350(2) -0.00674(14) -0.01208(15) -0.00356(14) O1 0.0219(4) 0.0516(6) 0.0385(5) -0.0056(4) -0.0134(4) -0.0021(4) O2 0.0296(5) 0.1011(10) 0.0487(7) -0.0306(7) -0.0109(5) 0.0092(6) O3 0.0507(7) 0.0480(7) 0.0885(10) 0.0227(6) -0.0396(7) -0.0125(5) O4 0.0312(5) 0.0394(6) 0.0753(8) 0.0092(5) -0.0269(5) -0.0118(4) C1 0.0426(7) 0.0298(6) 0.0394(7) 0.0040(5) -0.0231(6) -0.0119(5) C2 0.0250(5) 0.0278(6) 0.0268(6) 0.0000(5) -0.0122(5) -0.0051(4) C3 0.0265(6) 0.0233(5) 0.0304(6) 0.0006(4) -0.0145(5) -0.0065(4) C4 0.0318(6) 0.0238(6) 0.0302(6) -0.0003(4) -0.0154(5) -0.0071(5) C5 0.0427(7) 0.0284(6) 0.0306(6) -0.0003(5) -0.0180(6) -0.0078(5) C6 0.0502(8) 0.0317(7) 0.0406(7) 0.0033(5) -0.0312(7) -0.0082(6) C7 0.0347(7) 0.0319(7) 0.0456(8) 0.0020(6) -0.0254(6) -0.0056(5) C8 0.0274(6) 0.0294(6) 0.0338(7) -0.0001(5) -0.0146(5) -0.0066(5) C9 0.0262(6) 0.0472(8) 0.0361(7) -0.0074(6) -0.0118(5) -0.0032(5) C10 0.0231(5) 0.0316(6) 0.0287(6) -0.0022(5) -0.0106(5) -0.0061(5) C11 0.0287(6) 0.0423(7) 0.0263(6) -0.0033(5) -0.0100(5) -0.0097(5) C12 0.0421(8) 0.0585(9) 0.0291(7) 0.0078(6) -0.0115(6) -0.0239(7) C13 0.0484(8) 0.0430(8) 0.0431(8) 0.0127(6) -0.0238(7) -0.0242(7) C14 0.0333(6) 0.0374(7) 0.0257(6) 0.0006(5) -0.0142(5) -0.0099(5) C15 0.0309(7) 0.0527(9) 0.0698(11) 0.0040(8) -0.0252(7) -0.0129(6) C16 0.0420(8) 0.0319(8) 0.0822(13) -0.0018(8) -0.0291(8) -0.0001(6) C17 0.0381(7) 0.0399(8) 0.0539(9) -0.0021(6) -0.0215(7) -0.0107(6) C18 0.0381(8) 0.0979(15) 0.0440(9) -0.0251(9) -0.0076(7) -0.0040(9) _refine_ls_extinction_coef 280(50) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Si1 . C4 . 1.8944(13) yes Si1 . C16 . 1.8638(17) yes Si1 . C17 . 1.8703(15) yes Si1 . C18 . 1.8579(18) yes O1 . C8 . 1.3954(16) yes O1 . C9 . 1.3694(17) yes O2 . C9 . 1.1925(17) yes O3 . C14 . 1.1915(17) yes O4 . C14 . 1.3272(16) yes O4 . C15 . 1.4505(17) yes C1 . C2 . 1.5183(17) yes C1 . C13 . 1.324(2) yes C1 . H11 . 1.000 no C2 . C3 . 1.5125(16) yes C2 . C10 . 1.5296(17) yes C2 . H21 . 1.000 no C3 . C4 . 1.4092(17) yes C3 . C8 . 1.3909(17) yes C4 . C5 . 1.4041(17) yes C5 . C6 . 1.391(2) yes C5 . H51 . 1.000 no C6 . C7 . 1.380(2) yes C6 . H61 . 1.000 no C7 . C8 . 1.3839(18) yes C7 . H71 . 1.000 no C9 . C10 . 1.5154(17) yes C10 . C11 . 1.5436(17) yes C10 . H101 . 1.000 no C11 . C12 . 1.5326(19) yes C11 . C14 . 1.5199(18) yes C11 . H111 . 1.000 no C12 . C13 . 1.501(2) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C13 . H131 . 1.000 no C15 . H151 . 1.000 no C15 . H152 . 1.000 no C15 . H153 . 1.000 no C16 . H161 . 1.000 no C16 . H162 . 1.000 no C16 . H163 . 1.000 no C17 . H171 . 1.000 no C17 . H172 . 1.000 no C17 . H173 . 1.000 no C18 . H181 . 1.000 no C18 . H182 . 1.000 no C18 . H183 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C4 . Si1 . C16 . 110.76(7) yes C4 . Si1 . C17 . 109.69(6) yes C16 . Si1 . C17 . 111.35(8) yes C4 . Si1 . C18 . 108.96(7) yes C16 . Si1 . C18 . 108.64(10) yes C17 . Si1 . C18 . 107.35(8) yes C8 . O1 . C9 . 121.09(10) yes C14 . O4 . C15 . 117.07(11) yes C2 . C1 . C13 . 122.88(13) yes C2 . C1 . H11 . 118.558 no C13 . C1 . H11 . 118.558 no C1 . C2 . C3 . 111.01(10) yes C1 . C2 . C10 . 109.61(10) yes C3 . C2 . C10 . 109.53(10) yes C1 . C2 . H21 . 108.362 no C3 . C2 . H21 . 108.441 no C10 . C2 . H21 . 109.873 no C2 . C3 . C4 . 124.43(11) yes C2 . C3 . C8 . 116.48(11) yes C4 . C3 . C8 . 119.07(11) yes C3 . C4 . Si1 . 123.90(9) yes C3 . C4 . C5 . 117.52(12) yes Si1 . C4 . C5 . 118.57(10) yes C4 . C5 . C6 . 121.93(13) yes C4 . C5 . H51 . 119.034 no C6 . C5 . H51 . 119.035 no C5 . C6 . C7 . 120.19(12) yes C5 . C6 . H61 . 119.904 no C7 . C6 . H61 . 119.905 no C6 . C7 . C8 . 118.28(12) yes C6 . C7 . H71 . 120.860 no C8 . C7 . H71 . 120.860 no O1 . C8 . C3 . 121.79(11) yes O1 . C8 . C7 . 115.38(11) yes C3 . C8 . C7 . 122.81(12) yes O1 . C9 . O2 . 117.07(12) yes O1 . C9 . C10 . 117.84(11) yes O2 . C9 . C10 . 125.08(13) yes C2 . C10 . C9 . 111.58(10) yes C2 . C10 . C11 . 111.13(10) yes C9 . C10 . C11 . 108.83(10) yes C2 . C10 . H101 . 106.661 no C9 . C10 . H101 . 109.055 no C11 . C10 . H101 . 109.526 no C10 . C11 . C12 . 110.62(11) yes C10 . C11 . C14 . 109.56(10) yes C12 . C11 . C14 . 111.52(12) yes C10 . C11 . H111 . 109.362 no C12 . C11 . H111 . 107.307 no C14 . C11 . H111 . 108.408 no C11 . C12 . C13 . 112.68(11) yes C11 . C12 . H121 . 108.658 no C13 . C12 . H121 . 108.660 no C11 . C12 . H122 . 108.667 no C13 . C12 . H122 . 108.667 no H121 . C12 . H122 . 109.467 no C12 . C13 . C1 . 124.99(13) yes C12 . C13 . H131 . 117.505 no C1 . C13 . H131 . 117.508 no C11 . C14 . O4 . 110.99(11) yes C11 . C14 . O3 . 125.55(13) yes O4 . C14 . O3 . 123.44(13) yes O4 . C15 . H151 . 109.466 no O4 . C15 . H152 . 109.469 no H151 . C15 . H152 . 109.476 no O4 . C15 . H153 . 109.465 no H151 . C15 . H153 . 109.476 no H152 . C15 . H153 . 109.476 no Si1 . C16 . H161 . 109.467 no Si1 . C16 . H162 . 109.466 no H161 . C16 . H162 . 109.476 no Si1 . C16 . H163 . 109.467 no H161 . C16 . H163 . 109.476 no H162 . C16 . H163 . 109.476 no Si1 . C17 . H171 . 109.467 no Si1 . C17 . H172 . 109.467 no H171 . C17 . H172 . 109.476 no Si1 . C17 . H173 . 109.466 no H171 . C17 . H173 . 109.476 no H172 . C17 . H173 . 109.476 no Si1 . C18 . H181 . 109.467 no Si1 . C18 . H182 . 109.466 no H181 . C18 . H182 . 109.476 no Si1 . C18 . H183 . 109.466 no H181 . C18 . H183 . 109.476 no H182 . C18 . H183 . 109.476 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C15 3.171(2) . 1_655 no O2 O2 3.339(2) . 2_765 no O2 C15 3.453(3) . 1_655 no O2 C15 3.481(3) . 2_665 no O3 C13 3.554(2) . 2_675 no O4 C6 3.301(2) . 2_666 no C6 C10 3.592(2) . 2_666 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Si1 C4 C3 C2 . . . . 6.8(2) no Si1 C4 C3 C8 . . . . -175.1(1) no Si1 C4 C5 C6 . . . . 178.9(1) no O1 C8 C3 C2 . . . . -4.8(2) no O1 C8 C3 C4 . . . . 177.0(1) no O1 C8 C7 C6 . . . . -179.9(1) no O1 C9 C10 C2 . . . . 29.6(2) no O1 C9 C10 C11 . . . . 152.6(1) no O2 C9 O1 C8 . . . . -172.1(1) no O2 C9 C10 C2 . . . . -151.4(2) no O2 C9 C10 C11 . . . . -28.4(2) no O3 C14 O4 C15 . . . . -0.9(2) no O3 C14 C11 C10 . . . . 117.5(2) no O3 C14 C11 C12 . . . . -5.3(2) no O4 C14 C11 C10 . . . . -63.7(2) no O4 C14 C11 C12 . . . . 173.5(1) no C1 C2 C3 C4 . . . . 97.0(1) no C1 C2 C3 C8 . . . . -81.1(1) no C1 C2 C10 C9 . . . . 70.8(2) no C1 C2 C10 C11 . . . . -50.9(2) no C1 C13 C12 C11 . . . . 6.7(2) no C2 C1 C13 C12 . . . . 2.3(3) no C2 C3 C4 C5 . . . . -174.3(1) no C2 C3 C8 C7 . . . . 173.3(1) no C2 C10 C11 C12 . . . . 61.1(1) no C2 C10 C11 C14 . . . . -62.2(1) no C3 C2 C1 C13 . . . . 141.3(2) no C3 C2 C10 C9 . . . . -51.2(1) no C3 C2 C10 C11 . . . . -172.9(1) no C3 C4 Si1 C16 . . . . -62.2(1) no C3 C4 Si1 C17 . . . . 61.1(1) no C3 C4 Si1 C18 . . . . 178.4(1) no C3 C4 C5 C6 . . . . 0.0(2) no C3 C8 O1 C9 . . . . -21.0(2) no C3 C8 C7 C6 . . . . 1.9(2) no C4 C3 C2 C10 . . . . -141.8(1) no C4 C3 C8 C7 . . . . -4.9(2) no C4 C5 C6 C7 . . . . -3.0(2) no C5 C4 Si1 C16 . . . . 119.0(1) no C5 C4 Si1 C17 . . . . -117.7(1) no C5 C4 Si1 C18 . . . . -0.5(1) no C5 C4 C3 C8 . . . . 3.8(2) no C5 C6 C7 C8 . . . . 2.0(2) no C7 C8 O1 C9 . . . . 160.7(1) no C8 O1 C9 C10 . . . . 7.0(2) no C8 C3 C2 C10 . . . . 40.1(2) no C9 C10 C11 C12 . . . . -62.1(1) no C9 C10 C11 C14 . . . . 174.5(1) no C10 C2 C1 C13 . . . . 20.1(2) no C10 C11 C12 C13 . . . . -37.3(2) no C11 C14 O4 C15 . . . . -179.7(1) no C13 C12 C11 C14 . . . . 84.9(2) no #------------------------------------------------------------------------------ #===END data_she0715 # # 1. SUBMISSION DETAILS _publ_requested_journal Org.Biomol.Chem. _publ_contact_author_name ' Michael S. Sherburn ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_author_email 'sherburn@rsc.anu.edu.au ' _publ_contact_author_phone ' 61 2 6125 4988 ' _publ_contact_author_fax ' 61 2 6125 8114 ' loop_ _publ_author_name _publ_author_address 'Pearson, Emma L.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Willis, Anthony C.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Sherburn, Michael S.' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; 'Paddon-Row, Michael N.' ; School of Chemistry, University of New South Wales, Sydney, N. S. W. 2052, Australia ; _audit_creation_date 07-07-25 _audit_creation_method CRYSTALS_ver_12.18 _audit_update_record ; 2007-07-25 - Report on C16 H12 O6 by Anthony C. Willis for Emma Pearson and Mick Sherburn 2007-07-26 - passes checkcif tests with minor warnings ; _oxford_structure_analysis_title 'transformed -khl' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 11.7777(5) _cell_length_b 5.4798(1) _cell_length_c 20.1905(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1303.08(7) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,z+1/2 x+1/2,-y+1/2,z -x,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C16 H12 O6 # Dc = 1.53 Fooo = 624.00 Mu = 1.19 M = 300.27 # Found Formula = C16 H12 O6 # Dc = 1.53 FOOO = 624.00 Mu = 1.19 M = 300.27 _chemical_formula_sum 'C16 H12 O6' _chemical_formula_moiety 'C16 H12 O6' _chemical_compound_source local _chemical_formula_weight 300.27 _cell_measurement_reflns_used 11690 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 200 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min .14 _exptl_crystal_size_mid .34 _exptl_crystal_size_max .40 _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.119 # Sheldrick geometric approximatio 1.00 1.00 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.080 0 -1 0 0.030 -1 0 0 0.240 1 0 0 0.260 0 0 1 0.070 0 0 -1 0.030 0 -3 3 0.060 0 3 -3 0.060 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.053 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 1.6 deg at rate 48 sec/frame, crystal-detector distance 40mm, multiple scan sets so over 90 percent of data collected with 4-fold redundancy or more [assuming Friedel's Law]. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Watkin et al 2003)' _computing_publication_material 'CRYSTALS (Watkin et al 2003)' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 14752 _reflns_number_total 1527 _diffrn_reflns_av_R_equivalents 0.033 # Number of reflections with Friedels Law is 1527 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1491 _diffrn_reflns_theta_min 3.460 _diffrn_reflns_theta_max 27.463 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.463 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min 0 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _oxford_diffrn_Wilson_B_factor 2.38 _oxford_diffrn_Wilson_scale 1.09 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.13 _refine_diff_density_max 0.16 _refine_ls_number_reflns 1370 _refine_ls_number_restraints 1 _refine_ls_number_parameters 199 #_refine_ls_R_factor_ref 0.0260 _refine_ls_wR_factor_ref 0.0312 _refine_ls_goodness_of_fit_ref 1.1445 #_reflns_number_all 1523 _refine_ls_R_factor_all 0.0300 _refine_ls_wR_factor_all 0.0333 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1370 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_gt 0.0312 _refine_ls_shift/su_max 0.000281 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.703 0.293 0.478 ; _publ_requested_category ' fo ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Controlling cis/trans-selectivity in intramolecular Diels--Alder reactions of benzo-tethered, ester linked 1,3,9-decatrienes ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~18~H~22~O~4~Si is reported. ; _publ_section_comment #Text of the paper ; The space group is noncentrosymmetric but the anomolous dispersion terms are very small for all elements in the structure, so the absolute structure of the crystal can not be determined in this experiment. Consequently Friedel-pair reflections have been averaged and the Flack parameter has not been refined. The space group is not enantiomorphic so the compound is present as a racemate within the crystal structure. The crystallographic asymmetric unit consists of one C~16~H~12~O~6~ molecule. The largest features in a final difference electron density map are located along C---C bonds and have no chemical significance. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; Hydrogen atoms were observed in difference electron density maps prior to their inclusion. They were introduced at calculated positions and during refinement they ride of the atom to which they are attached. ; _publ_section_exptl_prep ; The compound was prepared by ELP and recrystallized from methanol. The sample id. was EP-I-27at02. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Mackay, S., Gilmore, C. J., Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.85768(10) 0.3658(2) 0.59102(9) 0.0297 1.0000 Uani . . . . . . C2 C 0.86869(13) 0.2318(3) 0.53389(11) 0.0266 1.0000 Uani . . . . . . O3 O 0.93969(11) 0.0748(2) 0.53410(10) 0.0344 1.0000 Uani . . . . . . C4 C 0.79526(13) 0.2947(3) 0.47672(11) 0.0238 1.0000 Uani . . . . . . C5 C 0.82351(14) 0.2226(3) 0.41610(11) 0.0278 1.0000 Uani . . . . . . C6 C 0.76126(16) 0.2998(3) 0.35447(11) 0.0304 1.0000 Uani . . . . . . C7 C 0.64850(14) 0.4347(3) 0.36803(10) 0.0253 1.0000 Uani . . . . . . C8 C 0.61265(15) 0.5762(3) 0.30716(10) 0.0287 1.0000 Uani . . . . . . O9 O 0.66335(13) 0.7514(3) 0.28583(9) 0.0403 1.0000 Uani . . . . . . O10 O 0.52104(11) 0.4792(3) 0.27869(10) 0.0379 1.0000 Uani . . . . . . C11 C 0.4767(2) 0.6127(5) 0.22234(14) 0.0529 1.0000 Uani . . . . . . C12 C 0.66499(14) 0.6031(3) 0.42768(10) 0.0226 1.0000 Uani . . . . . . C13 C 0.69182(13) 0.4492(3) 0.48832(10) 0.0215 1.0000 Uani . . . . . . C14 C 0.56446(15) 0.7675(3) 0.44178(10) 0.0250 1.0000 Uani . . . . . . O15 O 0.48938(13) 0.8118(3) 0.40362(10) 0.0390 1.0000 Uani . . . . . . O16 O 0.56236(10) 0.8824(2) 0.50206(9) 0.0255 1.0000 Uani . . . . . . C17 C 0.64015(14) 0.8215(3) 0.55184(10) 0.0230 1.0000 Uani . . . . . . C18 C 0.70695(13) 0.6144(3) 0.54618(10) 0.0227 1.0000 Uani . . . . . . C19 C 0.78476(14) 0.5665(3) 0.59561(11) 0.0256 1.0000 Uani . . . . . . C20 C 0.79407(16) 0.7124(4) 0.65098(11) 0.0336 1.0000 Uani . . . . . . C21 C 0.72336(18) 0.9149(4) 0.65594(11) 0.0351 1.0000 Uani . . . . . . C22 C 0.64597(15) 0.9729(3) 0.60638(11) 0.0291 1.0000 Uani . . . . . . H51 H 0.88999 0.1106 0.41113 0.0334 1.0000 Uiso R . . . . . H61 H 0.81185 0.4108 0.32849 0.0365 1.0000 Uiso R . . . . . H62 H 0.74425 0.1507 0.32772 0.0365 1.0000 Uiso R . . . . . H71 H 0.58848 0.3118 0.37881 0.0304 1.0000 Uiso R . . . . . H111 H 0.4085 0.5263 0.20447 0.0635 1.0000 Uiso R . . . . . H112 H 0.4549 0.7811 0.23656 0.0635 1.0000 Uiso R . . . . . H113 H 0.5363 0.6229 0.18715 0.0635 1.0000 Uiso R . . . . . H121 H 0.73221 0.7094 0.41856 0.0271 1.0000 Uiso R . . . . . H131 H 0.62585 0.3391 0.49725 0.0257 1.0000 Uiso R . . . . . H201 H 0.85016 0.6736 0.68665 0.0403 1.0000 Uiso R . . . . . H211 H 0.72832 1.0213 0.69608 0.0421 1.0000 Uiso R . . . . . H221 H 0.59604 1.1199 0.61012 0.0350 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0267(5) 0.0305(6) 0.0317(6) 0.0037(5) -0.0046(5) 0.0044(5) C2 0.0188(7) 0.0270(8) 0.0339(8) 0.0035(7) 0.0019(6) -0.0008(6) O3 0.0254(6) 0.0336(6) 0.0441(7) 0.0070(6) 0.0001(5) 0.0079(5) C4 0.0205(7) 0.0197(7) 0.0312(8) 0.0021(6) -0.0003(6) 0.0017(6) C5 0.0238(7) 0.0240(7) 0.0358(9) -0.0005(7) 0.0044(6) 0.0017(6) C6 0.0323(8) 0.0298(8) 0.0291(8) -0.0056(7) 0.0029(7) 0.0060(8) C7 0.0274(7) 0.0233(7) 0.0253(8) -0.0012(6) 0.0006(6) 0.0000(6) C8 0.0316(8) 0.0294(8) 0.0251(8) -0.0041(6) 0.0016(6) 0.0020(7) O9 0.0510(8) 0.0371(7) 0.0327(7) 0.0071(6) -0.0006(6) -0.0069(7) O10 0.0380(7) 0.0416(7) 0.0343(6) 0.0043(6) -0.0102(6) -0.0036(6) C11 0.0512(13) 0.0660(15) 0.0416(12) 0.0132(11) -0.0154(11) 0.0041(11) C12 0.0238(7) 0.0199(7) 0.0241(7) 0.0002(6) -0.0003(5) 0.0015(6) C13 0.0203(6) 0.0186(6) 0.0255(7) 0.0011(6) 0.0001(5) -0.0009(6) C14 0.0301(8) 0.0202(7) 0.0248(8) -0.0011(6) -0.0004(6) 0.0028(6) O15 0.0444(7) 0.0400(7) 0.0325(7) -0.0057(6) -0.0103(6) 0.0192(6) O16 0.0285(6) 0.0216(5) 0.0265(6) -0.0035(4) -0.0024(5) 0.0057(5) C17 0.0242(7) 0.0214(7) 0.0232(8) 0.0007(6) 0.0001(6) -0.0024(6) C18 0.0233(7) 0.0219(7) 0.0228(7) 0.0007(6) 0.0005(6) -0.0020(6) C19 0.0241(7) 0.0242(7) 0.0285(8) 0.0014(6) -0.0008(6) -0.0029(6) C20 0.0347(9) 0.0404(10) 0.0257(8) 0.0003(7) -0.0056(7) -0.0013(8) C21 0.0418(10) 0.0364(9) 0.0270(9) -0.0084(8) -0.0016(8) -0.0038(8) C22 0.0321(8) 0.0262(8) 0.0291(8) -0.0045(7) 0.0023(7) 0.0002(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.959(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.373(2) yes O1 . C19 . 1.399(2) yes C2 . O3 . 1.200(2) yes C2 . C4 . 1.483(2) yes C4 . C5 . 1.329(3) yes C4 . C13 . 1.502(2) yes C5 . C6 . 1.505(3) yes C5 . H51 . 1.000 no C6 . C7 . 1.544(2) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C8 . 1.513(2) yes C7 . C12 . 1.530(2) yes C7 . H71 . 1.000 no C8 . O9 . 1.210(2) yes C8 . O10 . 1.333(2) yes O10 . C11 . 1.450(3) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no C11 . H113 . 1.000 no C12 . C13 . 1.520(2) yes C12 . C14 . 1.515(2) yes C12 . H121 . 1.000 no C13 . C18 . 1.489(2) yes C13 . H131 . 1.000 no C14 . O15 . 1.198(2) yes C14 . O16 . 1.371(2) yes O16 . C17 . 1.4004(19) yes C17 . C18 . 1.385(2) yes C17 . C22 . 1.381(2) yes C18 . C19 . 1.380(2) yes C19 . C20 . 1.379(3) yes C20 . C21 . 1.391(3) yes C20 . H201 . 1.000 no C21 . C22 . 1.390(3) yes C21 . H211 . 1.000 no C22 . H221 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C19 . 122.27(13) yes O1 . C2 . O3 . 116.49(16) yes O1 . C2 . C4 . 118.33(14) yes O3 . C2 . C4 . 125.16(17) yes C2 . C4 . C5 . 120.13(15) yes C2 . C4 . C13 . 118.86(15) yes C5 . C4 . C13 . 120.96(15) yes C4 . C5 . C6 . 123.79(15) yes C4 . C5 . H51 . 118.1 no C6 . C5 . H51 . 118.1 no C5 . C6 . C7 . 114.01(15) yes C5 . C6 . H61 . 108.3 no C7 . C6 . H61 . 108.3 no C5 . C6 . H62 . 108.3 no C7 . C6 . H62 . 108.3 no H61 . C6 . H62 . 109.5 no C6 . C7 . C8 . 109.95(14) yes C6 . C7 . C12 . 108.61(14) yes C8 . C7 . C12 . 111.44(13) yes C6 . C7 . H71 . 108.9 no C8 . C7 . H71 . 108.9 no C12 . C7 . H71 . 108.9 no C7 . C8 . O9 . 123.93(16) yes C7 . C8 . O10 . 111.81(15) yes O9 . C8 . O10 . 124.22(17) yes C8 . O10 . C11 . 115.35(17) yes O10 . C11 . H111 . 109.5 no O10 . C11 . H112 . 109.5 no H111 . C11 . H112 . 109.5 no O10 . C11 . H113 . 109.5 no H111 . C11 . H113 . 109.5 no H112 . C11 . H113 . 109.5 no C7 . C12 . C13 . 109.00(13) yes C7 . C12 . C14 . 114.05(14) yes C13 . C12 . C14 . 109.95(13) yes C7 . C12 . H121 . 107.9 no C13 . C12 . H121 . 107.9 no C14 . C12 . H121 . 107.9 no C12 . C13 . C4 . 110.85(14) yes C12 . C13 . C18 . 108.62(12) yes C4 . C13 . C18 . 111.60(13) yes C12 . C13 . H131 . 108.6 no C4 . C13 . H131 . 108.6 no C18 . C13 . H131 . 108.6 no C12 . C14 . O15 . 125.22(15) yes C12 . C14 . O16 . 117.01(14) yes O15 . C14 . O16 . 117.70(15) yes C14 . O16 . C17 . 121.06(13) yes O16 . C17 . C18 . 120.51(14) yes O16 . C17 . C22 . 117.48(14) yes C18 . C17 . C22 . 122.01(16) yes C13 . C18 . C17 . 119.67(14) yes C13 . C18 . C19 . 122.08(14) yes C17 . C18 . C19 . 118.25(15) yes O1 . C19 . C18 . 120.64(15) yes O1 . C19 . C20 . 117.44(16) yes C18 . C19 . C20 . 121.92(16) yes C19 . C20 . C21 . 118.25(17) yes C19 . C20 . H201 . 120.9 no C21 . C20 . H201 . 120.9 no C20 . C21 . C22 . 121.54(17) yes C20 . C21 . H211 . 119.2 no C22 . C21 . H211 . 119.2 no C21 . C22 . C17 . 117.98(16) yes C21 . C22 . H221 . 121.0 no C17 . C22 . H221 . 121.0 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C21 3.213(2) . 1_545 no O1 O16 3.308(2) . 3_565 no O1 C22 3.309(2) . 1_545 no O1 C22 3.522(2) . 3_565 no O1 C11 3.572(3) . 2_645 no O3 O16 2.964(2) . 3 no O3 C14 3.025(2) . 3 no O3 C13 3.113(2) . 3 no O3 C17 3.228(2) . 3 no O3 C18 3.323(2) . 3 no O3 O16 3.369(2) . 3_565 no O3 O15 3.431(2) . 3 no O3 C20 3.529(3) . 1_545 no O3 C12 3.551(2) . 3 no O3 C19 3.554(2) . 1_545 no O9 C21 3.473(3) . 2_644 no O9 C6 3.504(2) . 1_565 no O15 C5 3.223(2) . 3_465 no O15 C4 3.472(2) . 3_465 no O15 C5 3.529(2) . 3_455 no O15 C6 3.568(2) . 3_465 no O16 C2 3.176(2) . 3_465 no O16 C13 3.471(2) . 1_565 no O16 C4 3.590(2) . 1_565 no C2 C22 3.322(2) . 1_545 no C2 C21 3.467(3) . 1_545 no C2 C17 3.526(2) . 1_545 no C4 C17 3.516(2) . 1_545 no C11 C22 3.567(3) . 4_674 no C13 C22 3.576(3) . 1_545 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C2 C4 C5 . . . . 160.6(2) no O1 C2 C4 C13 . . . . -16.9(2) no O1 C19 C18 C13 . . . . 3.8(3) no O1 C19 C18 C17 . . . . -177.3(2) no O1 C19 C20 C21 . . . . 179.1(2) no O3 C2 O1 C19 . . . . 174.7(2) no O3 C2 C4 C5 . . . . -17.7(3) no O3 C2 C4 C13 . . . . 164.8(2) no O9 C8 O10 C11 . . . . -6.0(3) no O9 C8 C7 C6 . . . . -67.5(2) no O9 C8 C7 C12 . . . . 53.0(2) no O10 C8 C7 C6 . . . . 110.2(2) no O10 C8 C7 C12 . . . . -129.3(2) no O15 C14 O16 C17 . . . . 173.3(2) no O15 C14 C12 C7 . . . . -17.1(3) no O15 C14 C12 C13 . . . . -139.9(2) no O16 C14 C12 C7 . . . . 165.9(1) no O16 C14 C12 C13 . . . . 43.1(2) no O16 C17 C18 C13 . . . . -3.0(2) no O16 C17 C18 C19 . . . . 178.0(2) no O16 C17 C22 C21 . . . . -179.7(2) no C2 O1 C19 C18 . . . . 10.6(2) no C2 O1 C19 C20 . . . . -169.3(2) no C2 C4 C5 C6 . . . . -173.3(2) no C2 C4 C13 C12 . . . . 149.5(1) no C2 C4 C13 C18 . . . . 28.3(2) no C4 C2 O1 C19 . . . . -3.7(2) no C4 C5 C6 C7 . . . . -10.1(2) no C4 C13 C12 C7 . . . . 57.4(2) no C4 C13 C12 C14 . . . . -176.9(1) no C4 C13 C18 C17 . . . . 158.7(2) no C4 C13 C18 C19 . . . . -22.3(2) no C5 C4 C13 C12 . . . . -27.9(2) no C5 C4 C13 C18 . . . . -149.2(2) no C5 C6 C7 C8 . . . . 161.2(1) no C5 C6 C7 C12 . . . . 39.0(2) no C6 C5 C4 C13 . . . . 4.1(3) no C6 C7 C12 C13 . . . . -63.1(2) no C6 C7 C12 C14 . . . . 173.6(1) no C7 C8 O10 C11 . . . . 176.3(2) no C7 C12 C13 C18 . . . . -179.6(1) no C8 C7 C12 C13 . . . . 175.6(1) no C8 C7 C12 C14 . . . . 52.3(2) no C12 C13 C18 C17 . . . . 36.2(2) no C12 C13 C18 C19 . . . . -144.8(2) no C12 C14 O16 C17 . . . . -9.5(2) no C13 C18 C17 C22 . . . . 176.1(2) no C13 C18 C19 C20 . . . . -176.2(2) no C14 O16 C17 C18 . . . . -12.1(2) no C14 O16 C17 C22 . . . . 168.8(2) no C14 C12 C13 C18 . . . . -53.9(2) no C17 C18 C19 C20 . . . . 2.7(3) no C17 C22 C21 C20 . . . . 0.7(3) no C18 C17 C22 C21 . . . . 1.3(3) no C18 C19 C20 C21 . . . . -0.9(3) no C19 C18 C17 C22 . . . . -2.9(3) no C19 C20 C21 C22 . . . . -0.8(3) no #------------------------------------------------------------------------------ #===END